Sodium borohydride → (2alpha,3alpha,5alpha,17beta)-2,3-Epoxyandrostan-17-ol

Participants

Reaction Steps

A solution of sodium borohydride (600 mg.) in ice-cold methanol (10 ml.) is added to a solution of 2α,3α-epoxy-5α-androstan-17-one (U.S. Pat. No. 3,169,136, Example I, 1.34 g.) in methanol (60 ml.) and the mixture is stirred at 0° for 30 minutes. The mixture is washed with saline, dried over sodium sulfate and concentrated under reduced pressure to give a residue which is chromatographed on a silica gel column. Appropriate fractions (TLC) are pooled and concentrated to give 2α,3α-epoxy-17β-hydroxy-5α-androstane.

Provenance & Evidence