Diazomethane → 3alpha-Hydroxy-17beta-methoxycarbonyl-5alpha-androstan-11-one

Participants

Reaction Steps

A solution of 3α-hydroxy-11-oxo-5α-androstane-17β-carboxylic acid (350 mg.) in methanol (20 ml.) and ether (10 ml.) was treated with a dry ethereal solution of diazomethane. After 10 minutes, any unreacted diazomethane was destroyed by the addition of a drop of glacial acetic acid and the mixture was evaporated to small bulk. This was taken up in ether and washed with dilute sodium hydrogen carbonate solution, with water, dried and evaporated to a foam. The product was crystallised from acetone and petrol to give title compound (28/ mg.) as off white needles; m.p. 162 163°; [α]D + 77°.

Provenance & Evidence