17-alkyl-20-keto substituted pregnenes, pregnadienes and methods of preparing the same

The invention comprises a compound of the formula: wherein R is an alkyl radical, R1 is hydrogen, hydroxyl or alkanoyloxy radicals; R2 is hydrogen, lower alkyl or chlorine and is a radical selected from the group consisting of: and when then R1 is hydrogen and when: then R1 is hydrogen, and a process for the preparation thereof by contacting a 17a -alkylpregn - 4 - ene - 3,20 - dione or 17a - alkylpregna - 4,6 - diene - 3,20 - dione with a metal borohydride in the presence of an alcohol to produce the corresponding 3-hydroxy derivative, and thereafter, if desired, performing the following further reactions on the 3-hydroxy product (a) reacting with an alkanoylating agent to produce the corresponding 3-alkanoyloxy derivative, (b) reacting with acetic acid to form the corresponding 3-unsubstituted derivative. Compounds having the formula: wherein R and R3 are alkyl radicals and R4 is hydrogen or a lower alkyl radical are obtained by reacting the corresponding D 5-3b -ols with potassium-t-butoxide and an alkyl halide. In cases where the 20-keto group undergoes reduction it may be regenerated with chromium trioxide.