Diazomethane → HCID 12836874, compound

Participants

Reaction Steps

Ethereal diazomethane (40 ml. generated from 3 g. of N-methyl-N'-nitro-N-nitrosoguinidine) is added to a mixture of 17β-methoxy-5α-androst-1-en-3-one (IV, Example 23, 1.0 g.) and palladium diacetate (10 mg.) in diethyl ether (20 ml.). After a few hours the organic diluents are removed by reduced pressure and the residue is column chromatographed thru silica gel (100 g.) eluting by gradient between ethyl acetate:SSB (5:95, 5 l.) and ethyl acetate:SSB (20:80, 5 l.). The appropriate fractions (TLC) are pooled and concentrated to give the title compound, m.p. 114°-118°; MS (m/e) 316, 301, 269, and 243; NMR (CDCl3) 0.77, 0.97, 3.23 and 3.34 δ; CMR (CDCl3) 9.66 δ.

Provenance & Evidence