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Патент USA US3057891

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3,057,883
United States Patent O??ce
Patented Oct. 9, 1962
1
2
3357,8831
tenes, 2-hydroxymethyl-17/3-hydroxy-A2-androstenes, 2a
and Z?-hydroxymethyl-17,8-hydroxy-androstanes, of their
Z-CARBOXY-ANDROSTANE DERIVATIVES AND
17ot-alkyl, alkenyl and alkynyl substituted derivatives as
PROCESS THEREOF
Albert Bowers, John Edwards, and James C. Orr, all of 5 Well as of their corresponding 19-nor-analogs.
In copending patent application Serial No. 128,974,
Mexico City, Mexico, assignors to Syntex Corporation,
?led August 3, 1961, there is described the preparation of
a corporation of Panama
2-formyl-A2-androstenes starting from 2-alkoxymethylene
No Drawing. Filed Oct. 20, 1961, Ser. No. 146,456
Claims priority, appiication Mexico Apr. 4, 1961
23 Claims. (Cl. 260—397.1)
The present invention relates to certain new cyclo
pentanoperhydrophenanthrene derivatives and to a meth
od for the preparation of the same.
More particularly, our invention relates to the novel
derivatives of dihydroallotestosterone, 19-nor-dihydroallo
testosterone and of their l7a-alkyl, alkenyl or alkynyl
10 substituted derivatives, which upon reduction with a
double metal hydride afford the corresponding 2-hydroxy~
methyl compounds which, by acid treatment, give rise to
the formation of the 2-f0rmyl-A2-androstenes and 19-nor
androstenes.
20: and ZB-carboxy derivaives of androstan-17?-ol, and 15
By reduction of these compounds with lithium in liquid
to 2-carboxy-A2-androsten-175-01 which may further
ammonia there are obtained the Za-hYdI‘OXYm?thYl
possess a 17a-alkyl, alkenyl or alkynyl group; it also com
androstanes and 19-nor-androstanes. By catalytic hydro
prises the preparation of the esters of such compounds
genation of the 2-formyl—A2-androstenes and 19-nor-an
and the corresponding 19-nor derivatives.
drostenes, there are obtained the 2,3-hydroxymethyl com
Such compounds are powerful anabolic agents having 20 pounds, as has been described in detail in copending patent
a favorable anabolic-androgenic ratio; they stimulate the
application Serial No. 128,972, ?led August 3, 1961.
appetite, help to increase the protein metabolism and the
The 2 ~ hydroxymethyl - 17B _ hydroxy~A2-androstenes
deposition of calcium in the bone tissue; they further show
which may also be employed as starting materials for
anti-estrogenic activity, lower the chloesterol level in the
the preparation of the 2-carboxy-androstenes object of
blood, inhibit the scretion of gonadotrophins by the pit 25 our present invention, are obtained by reducing the 2
uitary gland and exhibit depressant action on the central
formyl-Az-androstenes with sodium borohydride, such as
nervous system.
has been described in the patent application Serial No.
The 17a-alkenyl and l7a-alkynyl compounds further
146,455 ?led of even date.
possess progestational activity.
The novel compounds object of our invention are ob
30
The novel compounds object of our present invention
tained by the method illustrated by the following series
are represented by the following formulas:
of reactions:
OR’
|_..Rg
R
j
35
N51“ A
__) Brow-Ll
tr
R
R3000 I
40
H
1
OR’
n
LnRg
R
i
45
OR‘
OR!
LR,
|__-R,
R3000 M
50
a
In the above formulas, R represents hydrogen or
methyl, R1 represents hydrogen or an acyl group derived
from a carboxylic acid of 1 to 12 carbon atoms; R2 rep— 55
resents hydrogen, a lower alkyl, alkenyl or alkynyl group
such as methyl, ethyl, propyl, vinyl, ethynyl or propynyl,
R3O0O—-
R
R3000
R
i
a...
i
:
H
IV
H
In
In the above formulas, R, R1, R2 and R3 have the same
meaning set forth previously.
and R3 represents hydrogen or a lower alkyl group such
as methyl, ethyl or propyl. The wavy line at C-2 indi
In practicing the process outlined above, an ester of 2
formyl-Az-androsten-175-01 or a 170t-S1lbSlIltllt6d deriva
tive thereof (I; R==methyl) or an ester of the latter is
cates the ot or [3 con?guration for the substituent at such
position.
The acyl groups referred to above derive from a car
boxylic acid of less than 12 carbon atoms, saturated or
subjected to direct oxidation with oxygen in the presence
of platinum oxide as catalyst to produce the 2-carboxy
unsaturated, of straight, branched, cyclic or mixed ali
compounds (II; R=methyl, R3=hydrogen). Adequate
phatic-cyclic chain, substituted or not with hydroxyl, 6 UK solvents for this oxidation are ethyl acetate, hexane,
methoxy, amino, halogen or other groups; typical such
butyl acetate or any other similar organic ester. The re
esters are the acetate, propionate, butyrate, valerate, hemi
action is preferably conducted at room temperature and
succinate, enanthate, caproate, benzoate, undecenoate,
atmospheric pressure, for a period of time between 72
trimethylacetate, phenoxyacetate, cyclopentylpropionate
and ,B-chloropropionate.
The novel compounds object of our invention are ob
tained by oxidation of 2-forrnyl-17B-hydroxy-A2-andros
and 100 hours or under pressure for 24 to 36 hours.
70
Alternatively, such oxidation may be carried out with
chromium trioxide in acetic acid or in acetone in sulfuric
acid medium.
~
3,057,883
3
4
chromic acid (prepared in 23% sulfuric acid) and the
The ester group at C-175 may be saponi?ed to give
mixture was kept for 1 hour at 0° C. At the end of this
time the mixture was poured into water and the precipi
tate formed was collected and washed with water. Crys
the corresponding l7?-alcohol (II; R, R1 and R3=hydro
gen), which may be esteri?ed with another acid anhydride
or chloride in pyridine solution for the unsubstituted com
pounds, or in benzene solution and in the presence of p
tallization from acetone a?orded 2-carboxy-l7m-methyl
A2-androsten-17B-ol.
toluenesulfonic acid for the 17a-alkyl, alkenyl and alkynyl
A mixture of 250 mg. of the above compound, 10 cc. of
acetic acid, 5 cc. of acetic anhydride and 250 mg. of
p-toluenesulfonic acid was kept at room temperature for
stones, in the presence of a palladium catalyst, such as
5 % palladium on charcoal, palladium on barium sulfate or 10 1 hour, poured into water, heated on the steam bath for
30 minutes to hoydrolyze the excess of reagent and the
10% palladium on calcium carbonate, and using as sol
precipitate
formed was collected and washed with water
vents ethyl acetate, methanol, ethanol, there are obtained
substituted derivatives.
By catalytic hydrogenation of the 2-carboxy-A2-andro
to neutral, thus giving the acetate of 2-carb0xy-17a
the ZB-carboxy derivatives (III; R=methyl; R1 and
methyl-Az-androsten-173-01.
R3=hydrogen).
By esteri?cation of the 2-carboxy compounds of For
mulas I1 and Ill (R=methyl; R1 and R3=hydrogen)
Example III
A solution of 1 g. of 2-carboxy-A2-androsten-173-01,
obtained in Example I, in 15 cc. of methanol was cooled
with a diazoalkane, such as diazomethane or diazoethane,
there are obtained the 2-carbalkoxy compounds (II and
to 0-5° C. and treated with an excess of an ether solution
of diazomethane, prepared from 5 g. of nitrosomethyl
20
esteri?cation with an acid anhydride or chloride, by the
III; R:=methyl, R1=hydrogen, R3=rnethyl or ethyl). By
urea; the mixture was kept overnight at 0° C., the excess
of diazomethane was destroyed with a few drops of acetic
acid and the solution was poured into water and extracted
methods set forth above, there are obtained the diesters.
By alkaline treatment of the Z?-carbalkoxy compounds,
there are obtained the Za-carbalkoxy derivatives (IV;
with methylene chloride; the organic phase was washed to
R=methyl, R3=methyl, ethyl)
neutral, dried and evaporated to dryness. Crystallization
In the same manner, the method just described is ap
of the residue from acetone-hexane yielded Z-carbometh
plied to the 2-formyl-l9-nor-A2-androstenes, thus produc
ing the 17-esters of Z-carboxy-19-nor-A2-androsten-17B
ol, the 17-esters of 2?-carboxy-l9-nor-androstan-17f3-ol,
oxy-A2-androsten-l7?-ol.
A solution of 250 mg. of the above ester in 1 cc. of pyr
idine was mixed with 0.5 cc. of benzoyl chloride and
heated on the steam bath for 1 hour, cooled and poured
into Water; the precipitate formed was collected and re
2-carboxy-17a-alkyl, Not-alkenyl and 17a-a1kynyl-19
nor-Alandrosten - 175 - ol, 2B-carboxy-17a-alkyl, 17a-al
kenyl and l7cc-alkynyl-19-nor-androstan-17?-ol, 2a and
25-carbalkoxy-19-nor-androstan-17B-ol, 2a and 2?-carb—
alkoxy-l7a-alkyl, Hot-alkenyl and 17a-alkynyl-l9-nor-an
crystallized from chloroform-methanol, thus furnishing
the beonzoate of 2-carbomethoxy-M-androsten-1713-01.
Example I V
drostan-l7B-ol, as well as the 17-este1's of the carbalkoxy
35
compounds.
A solution of 500 mg. of 2-formyl-17a-ethynyl-19-nor
Alternatively, the 20c- and ZB-carboxy derivatives of an
A2-androsten-175-o1 was treated with an excess of an 8 N
drostan-17B-ol, 19-nor-androstan-17?-ol as well as of their
solution of chromic acid in acetone, following the method
17a-alkyl, alkenyl and alkynyl substituted derivatives may
of Example II. There was thus obtained 2-carboxy-17a
be obtained by oxidation with chromic acid of the corre
sponding 2a and 2,8-hydroxymethyl compounds and/ or of 40
their esters.
The following examples serve to illustrate but are not
intended to limit the scope of the invention:
Example I
ethynyl»A2-19-nor-androsten-l7?-ol.
By treating the above compound with an excess of di
azomethane, in accordance with the method of the preced
ing example, there was obtained the methyl ester of 2-car
boxy-17a-ethynyl-19-nor~A2-androsten-175-01.
45
To a solution of 2.5 g. of the acetate of 2-formyl-A2
androsten-17?-ol, described in copending patent applica
tion Serial No. 128,974, ?led August 3, 1961, in 250 cc.
of ethyl acetate was added 400 mg. of platinum oxide and
the mixture was stirred under an atmosphere of oxygen,
at atmospheric pressure and room temperature, for 80
A mixture of 250 mg. of the above methyl ester, 15 cc.
of benzene, 1 cc. of acetic anhydride and 500 mg. of
p-toluenesulfonic acid was kept at room temperature for
48 hours and then diluted with water; the benzene layer
was separated, successively washed with 5% sodium car
bonate solution and water, dried over anhydrous sodium
sulfate and evaporated to dryness under reduced pressure.
By chromatography of the residue followed by crystalliza
hours. The catalyst was removed by ?ltration through
celite and the solvent was evaporated. Crystallization of
tion of the solid fractions from acetone-ether, there was
obtained the acetate of 2-carbometh0xy-l7a-ethynyl-19
the residue from acetone-ether yielded the acetate of
2-carboxy-A2-androsten-175-01, M.P. 267—68° C., [a]D
nor-A2-androsten-17?-ol.
+67° (chloroform); 7x max. 218 mp, e 9100.
hydrides, there were obtained the caproate, propionate and
In the same manner, but using the respective acid an
A solution of 3 g. of the above compound in 100 cc.
cyclopentylpropionate of 2-carbomethoxy - 17a - ethynyl
of methanol was treated with 3 g. of potassium hydroxide
19-nor-A2-andr0sten-175-01.
dissolved in 5 cc. of water and 20 cc. of methanol, and the
Example V
mixture was kept overnight at room temperature, then 60
acidi?ed with acetic acid and concentrated to a small
A solution of 500 mg. of the caproate of 2-formyl-17a
volume. Water was added until complete precipitation
vinyl-az-androsten-176-01 in 65 cc. of ethyl acetate was
and the product was collected by ?ltration. Crystalliza
stirred for 75 hours under an atmosphere of oxygen and
tion from methylene chloride~hexane a?forded 2-carboxy
in the presence of 80 mg. of platinum oxide catalyst, at
A2-androsten-17?-ol, M.P. 243-244° C., A max. 219 11111.,
room temperature and atmospheric pressure; there was
5 8,700.
thus obtained the caproate of 2-carboxy-l7a-vinyl-Az-an
In the same manner the propionate of 2-formyl-19-nor
A2-androsten-17B-ol was converted into the propionate of
2-carboxy-19-nor-A2-androsten-17(3-01 and then into 2
carboxy-19-nor-A2-androsten-17,8-01.
drosten-17g8-ol.
By treating the above compound with an excess of di
70 azomethane, there was obtained the caproate of Z-carbo
Example 11
A stirred solution of 700 mg. of 2-formyl-l7a-methyl
A2-androsten-17?-ol in 10 cc. of pure acetone was cooled
to 0° C. and treated with 0.4 cc. of an 8 N solution of 75
methoxy-l7a-vinyl-A2-androsten-175-01.
Example VI
A stirred solution of 1.4 g. of 2-hydroxymethyl-17a
methyl-A2-androsten-1713-01, described in copending patent
3,057,883
5
application Serial No. 146,455 in 25 cc. of pure acetone
was collected, thus furnishing the acetate of Zea-carbo
was treated with 1.6 cc. of an 8 N solution of chromic
methoxy-androstan-175-ol.
acid, following the method described in Example II; there
By the same method but using caproic, undecenoic and
cyclopentylpropionic anhydrides as esterifying agents,
was thus obtained Z-carboxy-l7a-methyl-A2-androsten
175-o1, identical with that obtained in such example. By
there were obtained the caproate, undecenoate and cyclo
esteri?cation with an ether solution of diazoethane, there
pentylpropionate of Zea-carbomethoxy-androstan-175-o1.
Example XI
was obtained 2-car-boethoxy - 17a - methyl-Az-androsten
175-o1.
A solution of 1.2 g. of 2a-hydroxymethyl-17a-vinyl-19
Example VII
A stirred solution of 1 g. of the acetate of 25-hydroxy 10 nor-androstan-175-ol in 60 cc. of acetic acid was treated
with 0.6 g. of chromic acid in 15 cc. of acetic acid, in
methylandrostan-175-ol, obtained as described in the
accordance with the method of Example VII, thus giv
copending patent application Serial No. 128,972, in 50
iug 2a-carboxyl-17tx-vinyl-l9-nor-androstan-175-o1.
By
cc. of acetic acid was treated dropwise with a solution of
esterifying the above compound with acetic anhydride in
500 mg. of chromic acid in 10 cc. of 80% acetic acid,
benzene
solution and in the presence of p-toluenesulfonic
15
at a temperature between 15 and 20° C. The mixture
was kept for 2 hours at room temperature, then poured
into ice cold salt water and the precipitate formed was
collected and washed with water to neutral, thus giving
the acetate of 25-carboxy-androstan-175-o1, which was
puri?ed by crystallization from chloroform-methanol.
acid, there was obtained the acetate of 2a-carboxy-17a
vinyl-19-nor-androstan-175-o1.
20
The above compound was treated with an excess of
Example XII
By following the method of hydrogenation described
in Example X, l g. of 2-carboethoxy-17a-methyl-A2-an
drosten-175-ol, obtained as described in Example VI, was
diazornethane, thus yielding the respective methyl ester.
converted into 25 - carboethoxy - 17a - methyl-androstan
175-ol.
Example VIII
By following the method of the preceding example, 25
This compound was treated with a mixture of
25 acetic anhydride and acetic acid in the presence of p
methyl-l7u-ethynyl-androstan-175-o1, and 25-hydroxy
toluenesulfonic acid, in accordance with the method of
esteri?cation of Example II, and thus there was obtained
the acetate of 25-carboethoxy-17a-methyl-androstan
methyl-l7a-ethynyl-19-nor-androstan-175-ol were oxidized
175-o1.
hydroxymethyl-l7a-methyl-androstan-175-o1, 25-hydroxy
with an excess of chromic acid in acetic acid to produce, 30
respectively, 25-carboxyl-175-methyl-androstan - 175 - ol,
25-carboxy-17a-ethynyl-androstan - 175 - 01, and 25-car
boxy-l7a-ethynyl-19-nor-androstan-175-01.
Example XIII
2 g. of 2-hydroxymethyl-17a-ethyl-A2-androsten-175-o1
was oxidized with 8 N chromic acid in acetone, in ac
By treating
cordance with the method of Example VI to produce 2
these compounds with an ether solution of diazomethane,
there were obtained the respective methyl esters, which
were then esteri?ed with acetic anhydride in benzene solu
tion and in the presence of p-toluenesulfonic acid, thus
carboxy-17a-ethyl-A2-androsten-175-o1.
The above compound was hydrogenated in accordance
with the method of Example II, to produce 25-carboxy
17a-ethyl-androstan-175-o1.
giving ?nally the acetate of 25-carbomethoxy-l7a-methyl
The above compound was treated with an excess of
androstan-l75-ol, the acetate of 25-carbomethoxy-17a
in ether solution to yield 25-carbomethoxy
ethynylandrostan-175-ol and the acetate of 25-carbometh 4.0 diazornethane
17a-ethyl-androstan-175-01.
oxy-l7a-ethynyl-l9-nor-androstan-l75-ol.
A mixture of 800 mg. of the above methyl ester and 20
cc. of a 1% solution of sodium hydroxide in methanol
was kept at room temperature for 30 minutes and then
There was repeated the method of Example VI, but
poured into ice cold salt water. The product was ex
using 2a-hydroxymethyl-l7a-methyl-androstan-175-01 as 45 tracted with methylene chloride and the extract was
starting compound, thus obtaining 2u-carboxy-l7a-meth
washed with water to neutral, dried over anhydrous sodi
Example IX
yl-androstan-l75-ol and Zea-carbomethoxy-17a-methyl-an
um sulfate and evaporated to dryness, thus affording 2a
carbomethoxy-l7u-ethyl-androstan-175-o1.
drostan-l75-ol.
500 mg. of the above compound was esteri?ed with
By esterifying the above compound with cyclopentyl
propionic anhydride in benzene solution and in the pres 50 propionic anhydride in benzene solution and in the pres
ence of p-toluenesulfonic acid, by following the method
ence of p-toluenesulfonic acid, there was produced the
described in Example IV. There was thus obtained the
cyclopentylpropionate of 20a - carbomethoxy - 17cc - ethyl
propionate of 2-carbomethoxy - 17oz - methyl - androstan
175-o1.
Example X
androstan-17501.
55
Example XIV
By following the method of Example VI, 2a-hydroxy
A solution of 2 g. of the benzoate of Z-carbomethoxy
A2-androsten-l75-ol, obtained as described in Example
methyl-17a-ethynyl-19-nor-androstan-175-ol were oxidized
III, in 100 cc. of ethyl acetate was hydrogenated at room
with an excess of 8 N chromic acid in acetone, thus pro
methyl-17a-ethynyl-androstan - 175 - 01 and 2a - hydroxy
temperature and atmospheric pressure in the presence of 60 ducing 2a-carboxy-17a-ethynyl - androstan - 175-01 and its
19-nor derivative. By reacting these compounds with
200 mg. of 5% palladium on charcoal which had been
previously reduced. When the equivalent of 1.1 mols of
an ether solution of diazoethane, there were obtained the
hydrogen had been absorbed, the catalyst was removed
corresponding ethyl esters, i.e., 2ot-carboethoxy-17a
by ?ltration and the ?ltrate was evaporated to dryness.
ethynyl-androstan-175-ol and 2a-carboethoxy-l7a-ethynyl
Crystallization of the residue from chloroform-methanol 65 l9-nor-androstan-175-ol.
furnished the benzoate of 25-carbomethoxy-androstan
175-01.
Example XV
A solution of 1 g. of Z-carboxy-l9-nor-A2-androsten
The above compound was saponi?ed by following the
175-o1, obtained in Example I, in 75 cc. of methanol was
method of Example I, with simultaneous inversion of the
carboxyl group at C-2, thus producing Zea-carbometh 70 hydrogenated in the presence of 100 mg. of 5% palladium
oxy-androstan-175-ol.
on charcoal, following the method of Example X. There
A solution of 500 mg. of the above compound in 2
was thus obtained 25-carboxy-19-nor-androstan - 175 - 01,
cc. of pyridine was treated with 1 cc. of acetic anhydride
and the mixture was kept overnight at room tempera
produced 25-corbomethoxy-19-nor - androstan - 175 - ol.
ture. After pouring into water, the precipitate formed
Acetylation of this compound by conventional methods
which upon treatment with an excess of diazomethane
3,057,883
'8
. 2a~carboxy-19-nor4androstan-175-01.
. ZB-carboxy-l9-nor-androstan-17p-ol.
. 2u-carbomethoxy-17a-methyl-androstan-175-01.
furnished the acetate of ZB-carbomethoxy-19-n0r-andros
tan-l7l3-ol.
Example XVI
A mixture of 500 mg. of 2B-carbomethoxy-19-nor
. Z?-carbomethoxy-l9-nor-androstan~175-ol.
. 2a-carboethoxy-l7a-ethynyl-androstan-1713-01.
. A process for preparing a compound of the follow
androstan-l7B-ol and 15‘ cc. of a 1% solution of potas
sium hydroxide in methanol was kept at room tempera
ture for 1 hour, then poured into water and the precipitate
ing formula:
formed was collected, thus yielding 2oc-carbomethoxy-l9
10
nor-androstan-l7/3-ol.
By esteri?cation of the ‘above compound with benzoyl
R
HOOCMV ‘
chloride in pyridine, in accordance with the method de
scribed in Example III, there was obtained the benzoate
of 2or-carbomethoxy-19-nor-androstan-175-01.
‘
15
We claim:
1. A compound of the following formula:
wherein R is selected from the group consisting of hy
drogen and methyl; R1 is selected from the group con
sisting of hydrogen and a hydrocarbon carboxylic acyl
group of less than 12 carbon atoms; and R2 is selected
from the group consisting of hydrogen, lower alkyl,
lower alkenyl and lower alkynyl, comprising oxidizing a
R3000 I
C-l7-hydrocarbon carboxylic acid ester of the corre
sponding 2-hydroxymethyl-androstan-17,8-01 derivative
|
and thereafter saponifying the ester group.
23. A process for preparing a compound of the follow
wherein R is selected from the group consisting of hy
ing formula:
drogen and methyl; R1 is selected from the group consist
ing of hydrogen and a hydrocarbon carboxylic acyl group
of less than 12 carbon atoms; R2 is selected from the group 30
A
I
consisting of hydrogen, lower alkyl, lower alkenyl, and
lower alkynyl; and R3 is selected from the group con
sisting of hydrogen and lower alkyl.
2. 2-carboXy-A2-androsten-175-01.
3. The acetate of 2-carboxy-A2-androsten-175-01.
.
.
.
.
.
.
Z-carboxy-l9-nor-A2-androsten-l7?-ol.
Z-carboxy-l7a-methyl-A2-androsten-175-01.
2-carboxy-l7a-ethynyl-A2-androsten-173-01.
2-carboxy-17u-vinyl-A2-androsten-1713-01.
2-carbomethoxy-Az-androsten-l713-01.
The acetate of Z-carbomethoxy-l7a-ethynyl-A2- an
35
wherein R is selected from the group consisting of hy
drogen and methyl; R1 is selected from the group consist
40 ing of hydrogen and a hydrocarbon carboxylic acyl group
of less than 12 carbon atoms; R2 is selected from the
group consisting of hydrogen, lower alkyl, lower al
drosten-l7/3-ol.
kenyl and lower alkynyl ; and R3 is selected from the
10. The acetate of 2-carbomethoxy-l7a-methyl-A2
group consisting of hydrogen and lower alkyl, compris
androsten-17/3-ol.
ing oxidizing a compound of the following formula:
11. A compound of the following formula:
1mm
50
R3000 MN
RI
m‘
wherein R is selected from the group consisting of hydro 55 wherein R and R2 have the same meaning as above and
R4 represents the hydrocarbon carboxylic acyl group to
gen and methyl; R1 is selected from the group consisting
form the corresponding 2-carboxy-A2-andr0sten~175-01
of hydrogen and a hydrocarbon carboxylic acyl group of
l7-acylate derivative, hydrogenating the latter in the pres
less than 12 carbon atoms; R2 is selected from the group
ence of a hydrogenation catalyst to produce the corre
consisting of hydrogen, lower alkyl, lower alkenyl and
lower alkynyl and R3 is selected from the group consisting 60 sponding 2f3-carboxy-androstan-l75-01 compound, es
terifying the latter with a diazoalkane to produce the cor
of hydrogen and lower alkyl.
responding ZB-carboalkoxy-androstan-1713-01 compound
and then treating the latter with an alkali to produce the
corresponding 2u-carboalkoxy-androstan-173-01.
12. Zu-carboxy-androstan-175-01.
13. Z?-carboxy-androstan-17?-ol.
14. 2u-carboxy-17u-methyl-androstan-175-01.
l5. 2a-carboxy-17u-ethynyl-androstan-175-01.
l6. 2?-carboxy~17a-ethynyl-androstan-175-01.
65
No references cited.
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