GB801422A - Improvements in or relating to steroids and the manufacture thereof - Google Patents

Abstract

The invention comprises a 2,17-di-lower-alkyltestosterone having the formula: <FORM:0801422/IV (b)/1> wherein R is an alpha or beta-hydroxy or a keto group and R1 is hydrogen or the acyl radical of an organic carboxylic acid containing from 1-12 carbon atoms, inclusive and the lower alkyl group contains 1-8 carbon atoms, and the preparation thereof which comprises removing the 2-carbonyl group from a compound represented by the formula: <FORM:0801422/IV (b)/2> wherein R is hydroxy or keto, R1 is hydrogen or the acyl radical of an organic carboxylic acid, R11 is hydrogen, carbon-lower-alkoxy, lower alkoxy or trifluoromethyl and M is an alkali metal, with an alkali-metal lower alkoxide and an alkanol. Compound V is obtained by converting an 11-oxygenated 17-lower-alkyl-testosterone having the formula: <FORM:0801422/IV (b)/3> by glyoxylation, formylation, carboxylation or trifluoroacetylation to produce a 2-carbonyl derivative, alkylating to produce the corresponding 2-lower-alkyl-2-carbonyl compound, forming the alkali-metal salt thereof and removing the 2-carbonyl group. Examples describe the preparation of 2-methyl-11-b -hydroxy-17-methyltestosterone, the corresponding 11a -hydroxy and 11-keto compounds, the 2-ethyl- and 2-n-propyl compounds, 2-methyl 11b -hydroxy-17-methyltestosterone 17-acetate and 2 - methyl - 11b - hydroxy - 17 - methyltestosterone 17-propionate. Other 17-acylates may be formed with a lower aliphatic acid, a cyclic acid, a cycloaliphatic acid, an aryl or alkaryl acid, an aralkyl acid, a dibasic acid, an aminoacid, other heterosubstituted acids, a carbamic acid, or a heterocyclic acid. Specifications 724,094 and 750,941 are referred to.