Preparation of 16.alpha.-methyl steroids

Details Preparation of 16.alpha.-methyl steroids Preparation of 16.alpha.-methyl steroids

1994-01-12

1996-04-16

Hollinden, Gary E.

Organic compounds -- part of the class 532-570 series

Organic compounds

Cyclopentanohydrophenanthrene ring system containing

C07J 100

Patent

active

055084524

ABSTRACT:
A process for the preparation of a compound of the formula ##STR1## in which rings A and B are a remainder: ##STR2## in which the 3-ketone function is optionally protected in the form of a ketal, thioketal, hemithioketal or enol ether, or a remainder: ##STR3## wherein R is methyl or --CH.sub.2 --OR', R' is hydrogen or ether remainder or ester remainder, R.sub.1 and R.sub.2 together form a second bond, or R.sub.1 and R.sub.2 form together an epoxide in beta position, or R.sub.1 is hydrogen, ketone or .alpha.- or .beta.- hydroxy, free or protected in the form of an ether or ester and R.sub.2 is hydrogen, or R.sub.1 is hydrogen and R.sub.2 is .alpha.-hydroxy function, or R.sub.1 is .beta.-hydroxy, free or protected in the form of an ether or ester and R.sub.2 is .alpha.-fluorine or bromine and R.sub.3 is hydrogen or .alpha. or .beta. fluorine or methyl comprising reacting a compound of the formula ##STR4## in which A, B, R, R.sub.1, R.sub.2 and R.sub.3 have the above meaning with a methylation agent in the presence of a copper-based catalyst to form the 16 .alpha.-methylated enolate, hydrolyzing the latter to obtain the corresponding enol and reacting the latter with an oxidizing agent to obtain the compound of formula I.

REFERENCES:
patent: Re28369 (1975-03-01), Arth et al.
patent: 3080393 (1963-03-01), Stork et al.
patent: 4071624 (1978-01-01), Grunwell
patent: 4704455 (1987-11-01), Van Rheenen
patent: 4772755 (1988-09-01), Liotta
patent: 4929395 (1990-05-01), Van Rheenen
patent: 4990612 (1991-02-01), Van Rheenen
patent: 5149696 (1992-09-01), Claussner
Search Report No. 9300519 (for FR 9300519 21 Oct. 1993).
Fried, "Organic Reactions", Van Nostrand pp. 75-76 1972.

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