Hydrogen Bromide → 2beta-Bromo-17beta-cyano-3alpha-hydroxy-5alpha-androstan-11-one

Participants

Reaction Steps

Aqueous 48% hydrobromic acid (60 ml.) was added to a solution of 17β-cyano-2α,3α-epoxy-5α-androstan-11-one (3.03g.) in chloroform (175ml.) and the mixture stirred at room temperature for 1 hr. The organic phase was separated, washed with aqueous 10% sodium bicarbonate and water and dried. Filtration and evaporation followed by preparative t.l.c. afforded the pure title compound as a white froth (2.16g.); [α]D + 68.5°, (c 0.6).

Provenance & Evidence