Water → 3beta-Hydroxy-5beta-androstan-17-one

Participants

Reaction Steps

A solution of 7.6 parts of sodium hydroxide in 25 parts of water is added to a solution of 42.5 parts of 3β-acetoxy-5β-androstan-17-one in 140 parts of methanol with stirring. The resultant mixture is heated to reflux for 2 hours whereupon distillation is initiated and 109 parts of methanol are removed. The remaining methanol is removed by evaporation and the resulting crystalline solid is diluted with water and stirred. The crystals are collected by filtration, washed with water until the washings are about pH 6 and air-dried to afford, in 98.5% yield, 3β-hydroxy-5β-androstan-17-one. This compound melts at about 152°-155° C. and exhibits infrared absorption maxima in chloroform at 3620, 2940, 1735 cm-1 and is represented by the following structural formula. ##STR5##

Provenance & Evidence