GB801503A - Improvements in or relating to steroids and the manufacture thereof - Google Patents

Abstract

The invention comprises a 17a -methylandrostane 3,11b ,17b -triol of the formula: <FORM:0801503/IV (b)/1> wherein R is hydrogen or methyl, and a process which comprises reducing the 3-keto group to a hydroxy group in an 11b ,17b -dihydroxy-17a -alkyl 5a - (and 5b )-androstane-3-one or an 11b ,17b - dihydroxy - 17a - alkyl - 19 - nor - 5a -(and 5b -) androstane-3-one with a reducing agent to produce the corresponding 17a -alkyl-5a - (and 5b -) androstane-3,11b -17b -triol or 17a -alkyl - 19 - nor - 5a - (and 5b ) - androstane -3, 11b ,17b - triol. Reduction may be effected with sodium borohydride, potassium borohydride, lithium aluminium hydride, or other bimetallic hydride, sodium and alcohol. Alternatively hydrogen and a platinum catalyst may be employed. Examples describe the preparation of 17-methyl-5a (and 5b )-androstane-3b (and 3a ), 11b ,17b -triol, the corresponding 19-nor compounds, the 11,17- and 3,17-diesters thereof, e.g. formate, acetate, propionate, trimethylacetate, furoate, a or b -cyclohexyl propionate, benzoate, phenylacetate, a or b -cyclopentylpropionate, a or b -phenyl propionate, methyl benzoate, di-(a or b -furylacrylate, valerate and methacrylate, and the corresponding 17-monoesters and 3,11,17-triesters. Also mentioned are compounds in which the alkyl radical in position-17 is ethyl, propyl, isopropyl, butyl, sec.-butyl, hexyl, heptyl and octyl.