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Патент USA US3055930

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United States Patent O?tice
r
3,055,920
Patented Sept. 25, 1962
1
2
3,055,920
the 17m-alkyl, alkenyl or alkynyl substituted derivatives,
2~HYDR0XYMETHYL-A2-ANDR0STEN
DERIVA
TIVES AND PROCESS
as Well as of the corresponding l9-nor derivatives, there
Albert Bowers, John Edwards, and James C. Orr, all of
which upon subsequent esteri?cation produce the cor
are obtained the respective Z-hydroxymethyl compounds,
exico City, Mexico, assignors, by mesne assignments,
No Drawing. Filed Oct. 20, 1961, Ser. No. 146,455
Claims priority, application Mexico Feb. 23, 1961
17 Claims. (Cl. 260-397.5)
responding mono- or di-esters.
to Syntex Corporation, a corporation of Panama
The treatment of the l7-esters of 2-hydroxymethyl-A2
androsten-17?-ol, 2-hydroxymethyl-l9-n0r-A2-androsten
1713-01 or of the Not-substituted derivatives with an
etherifying agent gives rise to the formation of the 2
alkoXy and 2-aralkoxy compounds.
The present invention relates to certain new cyclo
The method described above for preparing the 2-hy
pentanoperhydrophenanthrene derivatives and to a
droxymethyl and 2-acyloxymethyl derivatives is illustrated
method for the preparation of the same.
More particularly, our invention relates to the novel
by the following sequence of reactions:
Z-hydroxymethyl, 2-alkoxymethyl, Z-aralkoxymethyl and
15
2 - acyloxymethyl derivatives of A2 - androsten-U?-ol,
which may further possess a 17a-alkyl, alkenyl or alkynyl
group; it also comprises the preparation of the esters of
such compounds and of the corresponding 19-nor-deriva
tives.
7
20
Such compounds are powerful anabolic agents having
a favorable anabolic-androgenic ratio; they help to in
crease the protein metabolism and the deposition of
calcium on the ‘bone tissue; furthermore they show anti
ono-
I
R
i
H
r
on
OH
|---R9
|---R?
i Homo
m
I
R
a
II
estrogenic activity, lower the cholesterol level in the blood 25
and inhibit the secretion of gonaldotropins by the
pituitary gland. The ?ee-alkenyl and Noe-alkynyl com
pounds further exhibit progestational activity.
The novel compounds object of our invention are
represented by the following formula:
30
mongo- )
OR1
R
WORM-L
to”
35
R
1'1
III
In the above formulas R, R1 and R2 have the same
meaning as set forth above; R4 represents and acyl radical
of less than 12 carbon atoms.
In practicing the process outlined above, Z-formyI-AZ
1'1
40
androsten-17,8~ol or one of the Not-substituted deriva
In the above formula R represents hydrogen or methyl;
tives thereof (I; R=Me) is subjected to reduction with a
R1 represents hydrogen or an acyl group derived from a
double metal hydride, such as sodium borohydride or
carboxylic acid of l to 12 carbon atoms; R2 represents
potassium borohydride, in a solvent inert to the reaction,
hydrogen, an alkyl, alkenyl or alkynyl group such as
such as methanol, tetrahydrofuran 0r dioxane, at room
methyl, ethyl, propyl, vinyl, ethynyl or propynyl, and R3
temperature for a prolonged period of time or under re
represents hydrogen, a lower alkyl group, a lower aralkyl
?ux for 1 hour, to produce the corresponding 2-hydroxy
methyl derivatives (II, R=Me). Esteri?cation of such
group of 1 to 8 carbon atoms or an acyl radical derived
from a carboxylic acid of 1 to 12 carbon atoms.
compounds with anhydrides or chlorides derived from
The acyl groups set forth above derive from carboxylic 50 carboxylic acids of 1 to 12 carbon atoms, in pyridine or
acids of less than 12 carbon atoms, saturated or un
benzene solution, produces the 2,17-diesters (III; R=Me,
R2=hydrogen) or 2-monoesters (III; R=Me, R2=alkyl,
saturated, of straight, branched, cyclic or mixed aliphatic
cyclic chain, substituted or not with groups such as hy
droxy, methoxy, amino, halogen or other groups; typical
such esters are the acetate, propionate, butyrate, valerate,
hemiscuccinate, enanthate, caproate, benzoate, undec
enoate, trimethylacetate, phenoxyacetate, cyclopentyl
propionate and B-chloropropionate.
alkenyl or alkynyl). The (3-2 monoesters may be esteri
tied at C-17 with the same or a different acid anhydride
55 or chloride of hydrocarbon carboxylic acids of less than
12 carbon atoms, in benzene solution and in the presence
of p-toluenesulfonic acid.
In the same manner, the process described above is
The novel compounds object of our invention are ob
tained from the 2-formyl-l7?-hydroxy-A2-androstenes and
the corresponding l9-nor derivatives.
In our copending patent application Serial No. 128,974,
?led August 3, 1961, there is described the preparation
of the Z-forrnyl-M-androstenes starting from a 2-alkoxy
methylene derivative of dihydroallotestosterone, 19-nor
dihydroallotestosterone or one of the 17a-alkyl, alkenyl
or alkynyl substituted derivatives, which by reduction
with a double metal hydride furnish the corresponding 3
hydroxy derivatives. By acid treatment of these com
applied to the Z-formyl-19-nor-A2-androstenes, thus pro
60
ducing Z-hydroxymethyl-19-nor-A2-androsten-17,8-01 and
the corresponding 17a-alkyl, alkenyl and alkynyl deriva
tives, as well as the mono- and diesters of such com
pounds.
Alternatively, there maybe employed as starting mate
65 rial and ester of 2-formyl-A2-androsten-175-01, of 2
formyl-19-nor-A2-androsten-l7B-ol or of the correspond
ing Nix-substituted derivatives, which on reduction with
a double alkali metal hydride in dioxane or tetrahydro
furan under anhydrous conditions, to avoid hydrolysis
pounds in the presence of a proton acceptor there are 70 of the acyloxy groups, produce the corresponding 17
obtained the 2-formyl-A2-androstenes.
,
esters of - 2'-hydroXymethy1-17?-hydroXy-A2-andr0stenes
and l9-nor-androstenes.
' '
By reduction of 2-formyl-A2-androsten-175-01, or of
The novel 2-alkoxy and 2-aralkoxy compounds object
3,055,920
of our invention are obtained by the method illustrated
by the following sequence of reactions:
OR1
R
HoHtc~
\
1'1
)2-
To a solution of 10 g. of 2-formyl-17a-methyl-A2-an
drosten-17l3-ol in 300 cc. of anhydrous tetrahydrofuran
was added 10 g. of sodium borohydride and the mixture
was stirred at room temperature for 24 hours; at the end
of this time the excess of reagent was destroyed with
. dim 5
Bionic-A
acetic acid, poured into ice water and the precipitate was
Crystallization from acetone-ether afforded 2
(/
1v
4
material, there was obtained 2~hydroxymethyl-19-nor-A2
androsten-17B-ol and its corresponding diacetate.
Example 111
10 collected.
hydroxymethyl - 17a - methyl - A2-androsten-17B-ol; M.P.
1'1
v
167—169° C.; [a]D+26° (chloroform).
In another experiment there was employed anhydrous
on
mm
as solvent, with the same result.
15 dioxane
A mixture of 1 g. of Z-hydroxymethyl-17a-methyl-A2
androsten-17?-ol, 10 cc. of pyridine and 1 cc. of acetyl
chloride was kept at room temperature for 36 hours and
then the solvent was evaporated under vacuum at a tem
perature below 60° C. Crystallization of the residue
from methylene chloride-hexane furnished 2-acetoxy
20
Bionic ‘/\a
methyl-17ot-methyl-A2-androsten-175-01.
Example IV
1'1
v1
In accordance with the method of reduction described
25 in the preceding example, there was treated 5 g. of 2
In the above formulas R, R1 and R2 have the same
formyl-17a-ethyl-A2-androsten-175-01 with sodium boro
hydride using tetrahydrofuran as solvent, thus yielding 2
meaning set forth previously; R5 represents a lower alkyl
hydroxymethyl-l7a-ethyl-A2-androsten-176-01.
or aralkyl group containing up to 8 carbon atoms.
In practicing the process just outlined, a l7-ester of
2-hydroxymethyl-A2-androsten-175-01, which may further
From a solution of 1 g. of the above compound in 130
cc. of benzene free of thiophene there was distilled ap
proximately 30 co. in order to remove moisture; there
was then added 0.52 cc. of pyridine and 1.5 cc. of un
decenoyl chloride and the mixture was re?uxed for 1
30
possess a substituent at C—l7oc of the type set forth above,
or ‘from the corresponding 19-nor derivatives (IV), is
allowed to react at room temperature with an excess of
an ether solution of a diazoalkane, such as diazomethane
or diazoethane, and in the presence of a catalyst, such
as boron tri?uoride or aluminum chloride, to produce the
35 hour; after evaporating to dryness under vacuum the
residue was chromatographed on 30 g. of washed alumina,
thus yielding Z-undecenoyloxymethyl-17a-ethyl-A2-an
drosten-17?-ol.
Z-methoxymethyl or 2-ethoxymethyl derivatives (V;
R5==methyl, ethyl). Saponi?cation of these compounds
by conventional methods produces the corresponding free
ethers (VI; R5=methyl, ethyl).
Example V
By following the method of reduction described in Ex
40
ample I, 2-formyl~17a-ethynyl-A2-andr0sten-175-01, 2
Alternatively, the etheri?cation may be effected by
reacting at the re?ux temperature the 2-hydroxymethyl
formyl-l7a-vinyl-A2-androsten-175-01, 2-formy1-17a-vinyl
19-nor-A2-androsten-17?-ol and 2-formyl-17a-ethynyl-19
compounds of Formula IV with an alkyl or aralkyl halide,
preferably with an alkyl or aralkyl iodide, in an organic 45 nor-A2-androsten-17B-ol were respectively converted into
2-hydroxymethyl-17a-ethynyl-dz-androsten-1713-01, 2-hy
solvent such as acetone and in the presence of a base,
droxymethyl - 17u-vinyl-A2-androsten-17,8-01, Z-hydroxy
such as potassium carbonate, or by treatment with an
methyl - 17a - vinyl-19-nor-A2-androsten-17,6-01 and 2-hy
alkyl sulfate in acetone solution and in the presence of
droxymethyl-17wethynyl-19-nor-A2-androsten-175-01.
a base, preferably potassium hydroxide, at room tempera
Example VI
ture.
50
' The following examples serve to illustrate but are not
intended to limit the present invention.
A solution of 500 mg. of 2-hydroxymethyl-A2-andro
sten-17B-ol in 2 cc. of pyridine was treated with 1 cc.
of caproic anhydride and the mixture was kept over
night at room temperature; it was then poured into water
A solution of 5 g. of Z-formyl-M-androsten-1713-01 in 55 and the precipitate formed was collected by ?ltration,
200 cc. of methanol was cooled to —5° C., treated with
thus affording the caproate of 2-capronoxyrnethyl-A2
1.5 g. of sodium borohydride in 30 cc. of methanol and
androsten-17?-ol.
the mixture was kept at room temperature for 1 hour
By the same method, but using propionic, valeric and
under anhydrous conditions; at the end of this time it
cyclopentylpropionic anhydride as esterifying agents,
Example I
was cooled, the excess of reagent was destroyed with a 60 there were obtained the corresponding diesters of 2-hy
few drops of glacial acetic acid and water was added
droxymethyl-A2-androsten-175-01.
until complete precipitation; the precipitate formed was
collected by ?ltration, washed and dried, thus yielding
Example VII
2-hydroxymethyl-A2-androsten-175-01; M.P. 193—194° C.,
[ethyl-65° (chloroform).
A mixture of 1 g. of the above compound, 4 cc. of
pyridine and 2 cc. of acetic anhydride was heated on
the steam bath for 1 hour, poured into water and the
precipitate formed was collected, washed with water to
neutral and dried. By crystallization from acetone
hexane there was obtained 2-acetoxymethyl-Alandrosten
175-01 acetate.
Example 11
By following the method of the preceding example,
A mixture of 1 g. of 2-hydroxymethyl-17a-methyl-A2
65 androsten-l7i-3-ol, 50 cc. of benzene, 2 cc. of acetic an
hydride 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, consecutively
washed with 5% sodium carbonate solution and with
70 water to neutral, dried over anhydrous sodium sulfate and
evaporated to dryness under reduced pressure. By
chromatography of the residue and crystallization of the
but using 2-formyl-19-nor-A2-androsten-173-01 as starting 75
solid fractions from acetone-ether there was obtained the
agetatle of 2 - acetoxymethyl-17a-rnethyl-A2-androsten
5,055,926
.
.
5
,1.
.
In the same manner, but employing propionic, caproic,
undecenoic and cyclopentylpropionic anhydrides as esteri
fying agents (the latter two being employed in twice the
amount), there were obtained the propionate of Z-propion
. I
6
Example XI
To a solution of 10 g. of 2-formyl-A2-androsten-17?-ol
in 40 cc. of pyridine was added 10 cc. of benzoyl chloride
and the mixture was heated on the steam bath for 1 hour,
cooled and poured into water; the precipitate formed was
oxymethyl-l7a-methyl-A2-androsten-17,6-01, the caproate
of 2 - capronoxymethyl - 17a-methyl-A2-and-rosten-175-01,
the undecenoate of Z-undecenoyloxymethyl-l7a-methyl~
collected and recrystallized from chloroform-methanol,
A2-androsten-17/3-ol and the cyclopentylpropionate of 2
thus yielding the benzoate of 2-formyl-A2-androsten
17,6-01.
cyclopentylpropionoxymethyl - 17a-methyl-A2-androsten
1718-01.
10
Example VIII
To a solution of 5 g. of the above benzoate in 100 cc.
out anhydrous dioxane was added 5 g. of potassium boro
hydride and :the mixture was stirred overnight at room
2 g. of 2-formyl-Not-methyl-19-nor-A2-androsten-1718-01
temperature and under anhydrous conditions; the excess
was reduced with sodium borohydride in tetrahydrofuran,
of reagent was destroyed with acetic acid, the mixture
following the method described in Example I; there was 15 was poured into water and the product extracted with
thus obtained 2-hydroxymethyl-17u-methyl-l9-nor-A2
ethyl acetate.
The organic extract was washed to neu
androsten-17/8-ol.
tral, dried and evaporated to dryness under vacuum.
The above compound was dissolved in 10 cc. of pyri
dine and 5 cc. of acetic anhydride, heated for 1 hour on
benzoate of 2~hydroxymethyI-AZ-androsten-175-01.
Crystallization from chloroform-methanol furnished the
the steam bath and poured into ice water; the precipi 20
By subsequent treatment with an excess of diazometh
tate Iformed was collected, thus giving Z-acetoxy-methyl
ane, in accordance with the method of Example X, there
Hot-methyl-19-nor-A2-androsten-l75-01.
was obtained the benzoate of 2-methoxymethyl-A2-andos~
500 mg. of the latter compound was treated with 1 cc.
ten-17?-ol.
'
--
a
-
of cyclopentylpropionic anhydride in benzene solution and
A solution of 500 mg. of the above compound in 25
in the presence of p-toluenesulfonic acid, in accordance 25 cc. of 2% methanolic potassium hydroxide solution was
with the method described in Example VII; there was thus
re?uxed for 2 hours, then neutralized with acetic acid,
obtained the cyclopentylpropionate of 2-acetoxymethyl
concentrated under vacuum to a small volume and poured
l7a-methyl-19-nor-androsten-1713-01.
into ice cold salt water; the precipitate formed was col—
lected, washed and dried, thus giving 2-methoxymethyl
Example IX
30
A2-androsten-17,B~ol.
A mixture of 5 g. of Z-formyl-17a-methyl-A2-androsten
Example XII
17,8-01, 200 cc. of acetic acid, 100 cc. of acetic anhy
dride and 5 g. of p-toluenesulfonic acid was kept at room
temperature for 1 hour, poured into water, stirred for
30 minutes to hydrolyze the excess of anhydride and ex
tracted several times with methylene chloride; the com~
There was repeated the process of the preceding exam
ple, but using the acetate of 2-formyl-19-nor-A2-andro
sten-17/3-o1 as starting material. There were thus suc
35 - cessively
obtained: the acetate of 2-hydroxymethyl-19~
bined extract was washed to neutral, dried over anhydrous
nor-A2-androsten-17/8-ol, the acetate of 2~methoxymethyl
sodium sulfate and evaporated to dryness. The residue
was dissolved in 100 cc. of 1% methanolic potassium hy
droxide, ‘kept at 0-10° C. for 1 hour, poured into Water
and extracted with ethyl acetate; the extract was washed
with water to neutral, dried over anhydrous sodium sul
fate and evaporated to dryness under vacuum. By crys
tallization ‘from acetone~hexane there was obtained the
A2-androsten-l7-ol.
acetate of 2-formyl-17m-mcthyl-nz-androsten-l7,8-01.
19-nor-A2-androsten-17a-o1 and 2-methoxymethyl-19-nor
Example XIII
1 g. of the caproate of Z-formyl-17a-vinyl-A2-andro
sten-17?-ol was reduced with sodium borohydride in di
oxane solution, in accordance with the method of Exam
45
The above compound was reduced with sodium boro
ple III, to produce the caproate of 2-hydroxymethyl-17a
vinyl-nz-androstend7,8-01.
A solution of 500 mg. of the above compound in 75
hydride in tetrahydrofuran, in accordance with the meth
od of Example III, to produce the acetate of 2-hydroxy
cc. of ether was treated with an ether solution of diazo
ethyl-Az-androsten-175-01.
androsten-17?-ol.
methane and 10 mg. of aluminum chloride; the mixture
was kept at room temperature for 1 hour, the excess of
By the same method 2-formyl~17a-ethyl-A2-androsten 50 diazomethane was destroyed by the addition of a ‘few
1718-01 was converted into the respective acetate which on
drops of acetic acid and evaporated to dryness, thus fur
reduction afforded the acetate of 2-hydroxymethyl-17a
nishing the caproate of Z-methoxymethyl-17a-vinyl-A3
methyl-1 7a-methyl-A2-androsten-175-01.
Example X
Exam‘ple XIV
v55
There was repeated the method of the preceding exam
A solution of 1 g. of the acetate of Z-hydroxymethyl
17a-methyl-A2-androsten-17,8-01 in 100 cc. of ether was
cooled to 0~5° C. and treated with an ether solution of
ple, but using as starting materials the acetate of 2-formyl
diazomethane (prepared from 5 g. of nitrosomethylurea) 60
and 3 drops of recently distilled boron tri?uoride etherate.
17a-ethynyl-A2-androsten-17,8-01 acetate, 2-methoxymeth~
yl-17ot-ethnyl~2-androsten-l7,8-01 acetate, 2-hydroxymeth
17a-ethynyl~A2-androsten-1713-01 and its corresponding
19-nor analog, thus giving respectively 2-hydroxymethyl
The mixture was kept at room temperature for 1 hour,
treated with a few drops of acetic acid to destroy the ex
2 - methoxymethyl - 17oz -
cess of diazomethane and then evaporated to dryness;
sten~17,B-ol acetate.
yl-l7ac-ethynyl-19-nor-A,2 androsten-17B-ol acetate and
there was thus obtained 2-methoxymethyl-17a-methyl-A2 65
androsten-lZB-ol, acetate.
ethynyl f 19 - nor - A2 - andro-'
Example XV
There was repeated the method of Example X, but em
ploying an ether solution of diazoethane instead of vdiazo
A solution of 500 mg. of the above compound in 50 cc.
of methanol was treated with 500 mg. of potassium hy
methane, thus obtaining the acetate of 2-ethoxymethyl
droxide dissolved in 1 cc. of water and 5 cc. of methanol
and the mixture was kept overnight at room temperature; 70 l7a-methyl-A2-androsten-175-01 and then the correspond
ing free compound.
it was then neutralized with acetic acid, concentrated to a
small volume and diluted with water until complete pre
Example XVI
cipitation. The product was collected by ?ltration and
A mixture of 2 g. of the acetate of Z-hydroxymethyl
crystallized from methylene chloride-hexane, thus afford
ing 2-methoxymethyl-l7a-methyl-A2~androsten-17/3-01.
17a-methyl-A2-androsten-175-01, 100 cc. of anhydrous
75 acetone, 10 cc. of methyl iodide and 2 g. of anhydrous
3,055,920
8
16. A process for preparing a compound of the fol
potassium carbonate was re?uxed for 48 hours. At the
end of this time it was poured into water, extracted with
ethyl acetate and the organic extract was washed with
water, dried over anhydrous sodium sulfate and evapo
lowing formula:
rd
rated to dryness under vacuum. The residue was puri
?ed by chromatography on washed alumina, thus fur
nishing the acetate of 2-methoxymethyl—17a-methy1-A2
androsten-17/3-ol, identical with the product obtained in
Example X.
10
Example XVII
wherein R is selected from the group consisting of hy
drogen and methyl; R1 is selected from the group con
By following the method of the preceding example, but
using ethyl, propyl or benzyl iodide instead of methyl
iodide, the acetate of 2-hydroxymethyl-17u-ethyl-A2-an 15
drosten-17B-ol was converted into 2-ethoxymethyl-17a
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 reacting a com
ethyl-A2-androsten-17B-ol acetate, 2-propoxymethyl-l7a
ethyl-M-androsten-U?-ol acetate and 2-benzoxymethyl
17a-ethyl-A2-androsten-1713-01 acetate. By subsequent
pound of the following formula:
saponi?cation of these compounds, in accordance with 20
the method of Example X, there were obtained the re
spective free compounds.
-6193
Exam'ple XVIII
By following the method of acetylation described in 25
Example III, 2-hydroxymethyl-17a-vinyl-A2-androsten
1719-01 and Z-hydroxymethyl-17a-ethynyl-A2-androsten
175-01 were respectively converted into 2-acetoxymethyl
17a-vinyl-A2-androsten-175-01 and 2-acetoxymethyl-17a
ethynyl-Az-androsten-175-01.
wherein R, R1 and R2 have the same meaning as above,
30 with a double metal hydride to form the corresponding
Z-hydroxymethyl compound and thereafter esterifying
We claim:
with a hydrocarbon carboxylic acid of less than 12 car
1. A compound of the following formula:
bon atoms.
17. A process for preparing a compound of the fol
ORl
35 lowing formula:
A. Hi”
weak/l1
40
IUOHaC-l
wherein R is selected from the group consisting of hydro 45
gen and methyl; R1 is selected from the group consisting
wherein R is selected from the group consisting of hy
of hydrogen and a hydrocarbon carboxylic acyl group of
drogen and methyl; R1 is selected from the Igroup con
less than 12 carbon atoms; ‘R2 is selected from the group
sisting of hydrogen and a hydrocarbon carboxylic acyl
consisting of hydrogen, lower alkyl, lower alkenyl and
group of less than 12 carbon atoms; R2 is selected from
lower alkynyl, and R3 is selected from the group con
the group consisting of hydrogen, lower alkyl, lower
sisting of hydrogen, lower alkyl and aralkyl containing up
alkenyl and lower alkynyl; and R5 is selected from the
group consisting of lower alkyl and aralkyl containing
to eight carbon atoms.
2. 2-hydroxymethyl-M-androsten-l76-01.
up to 8 carbon atoms comprising reacting a compound
3. 2-hydroxymethyl-17a-methyl-A2-androsten-l718-01.
of the following formula:
4. Z-hydroxymethyl-19-nor-A2-androsten-175-01.
5. Z-hydroxymethyl-17a-vinyl-Az-androsten-l75-01.
6. Z-hydroxymethyl-17u-ethynyl-A2-androsten-175-01.
55
l---.Rg
7. 2 - hydroxymethyl - 17a - methyl - 19 - nor - A2 - an
drosten-17/3-ol.
Ii
60
8. 2 - hydroxymethyl - 17oz - ethynyl - 19 - nor - A2 - an
drosten-l7p-ol.
'
9. The propionate of 2-propionoxymethyl-Az-andro
H
sten-17?-ol.
10. The caproate of Z-capronoxymethyl-M-androsten
175-01.
11. 2-methoxymethyl-A2-androsten-175-01.
12. Z-methoxymethyl-l7a-methyl-A2-androsten-17,6-01.
13. The acetate of 2-111eth0xymethyl-A2-androsten
17/3-01.
14. 2-acetoxymethyl-17a-vinyl-Az-androsten-17,6-01.
15. 2-acetoxymethyl-17a-ethynyl-A2-androsten-1713-01.
65 wherein R and R2 have the same meaning as before and
R1 represents the hydrocarbon carboxylic acyl group of
less than 12 carbon atoms, with a double metal hydride
to form the corresponding 2-hydroxymethyl compound
and thereafter reacting the latter compound with an
etherfying agent.
No references cited.
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