17beta,19-Dihydroxy-1alphamethyl-4-androsten-3-one → 17beta,19-Dihydroxy-1alpha-methyl-5-androsten-3-one

Participants

Reaction Steps

A solution of 17β,19-dihydroxy-1α-methyl-4-androsten-3-one in dimethylsulfoxide is added to a solution of potassium t-butoxide in dimethylsulfoxide precooled to 20° C. The reaction mixture is stirred under nitrogen for 10 minutes at room temperature and then poured onto ice cold aqueous ammonium chloride solution with vigorous stirring. The precipitate is rapidly filtered under vacuum, washed well with water and air dried. Crystallization of this residue from an acetone-hexane solution furnishes pure 17β,19-dihydroxy-1α-methyl-5-androsten-3-one.

Provenance & Evidence