Water → 17beta-Methylamino-androst-5-ene-3beta,16alpha-diol

Participants

Reaction Steps

Sodium hydroxide solution (1.63 ml; 4 N) was added to a solution of 17β-methylamino-androst-5-ene-3β,16α-diol 3-acetate (1.63 g) in ethanol (32.6 ml) and the resultant solution was refluxed for 1 h. Water (350 ml) was added and the precipitated crude product was filtered off and washed with water. The product was dissolved in a mixture of dichloromethane-methanol (≈1:1) and treated with charcoal. After filtration through dicalite, the filtrates were evaporated to dryness and the resultant offwhite solid was crystallised from methanol-dichloromethane-ether to give pure 17β-methylamino-androst-5-ene-3β,16α-diol as needles (1.25 g; 86.8%), m.p. 241°-246° C. (decomp.), [α]D -100.2° (c 0.93 in pyridine).

Provenance & Evidence