m-Chloroperbenzoic acid → 17beta-Cyano-2alpha,3alpha-epoxy-5alpha-androstan-11-one

Participants

Reaction Steps

A solution of 17β-cyano-5α-androst-2-en-11-one (2.8g.) and 85% m-chloroperbenzoic acid (2.0g.) in chloroform (50 ml.) was stirred for 1.5 hour at room temperature and then diluted with chloroform (75 ml.). This solution was washed with aqueous 10% sodium bicarbonate and water prior to drying. Filtration and evaporation afforded a solid (3.18g.) which was recrystallised from ether/petrol to afford the pure title compound; m.p. 206°-208°; [α]D + 93°, (c 0.7).

Provenance & Evidence