Perchloric Acid → 17alpha-Hydroxy-3-oxo-4-androstene-17-carboxylic acid amide

Participants

Reaction Conditions

Reaction Steps

A solution of 6.26 g of 17α-hydroxy-17-cyano-4-androsten-3-one in 50 ml of glacial acetic acid and 50 ml of acetic anhydride is combined with 0.5 ml of 70% perchloric acid, and the mixture is allowed to stand for 1 hour at 20° C. The product is precipitated into ice water, filtered off, and then dissolved in 570 ml of methanol. This solution is combined with 61 ml of a 1 N potassium hydroxide solution, and the mixture is stirred overnight at 20° C. The methanolic solution is diluted with 500 g of ice water, the precipitated product is vacuum-filtered and dried. Repeated crystallization from ethyl acetate--methylene chloride yields 5.62 g of 17α-hydroxy-3-oxo-4-androstene-17-carboxylic acid amide, mp 271°-273.5° C.

Provenance & Evidence