Studies on Steroids. XXXI

Reactions of N, N-Dibromobenzenesulfonamide on Cholesteryl Acetate

Abstract

Reaction of cholesteryl acetate with N, N-dibromobenzenesulfonamide (Dibrornamine-B) in dilute acetone containing some acetic acid gave two compounds, (A) and (B). (A), C₂₉H₄₉O₃Br, m.p. 175° (decomp.), [α]_D²⁰=-33.8° (yield, 37%), was established as 5α-bromocholestane-3β, 6β-diol 3-acetate from its acetyl derivative, oxidation product, debrominated product of the oxidation product, and the formation of a β-oxide compound by treating with alcoholic KOH. (B), C₂₉H₄₉O₃Br, m.p. 188° (decomp.), [α]_D³²=-34.7° (yield, 6%), was found to be 6β-bromocholestane-3β, 5α-diol 3-acetate from the properties of the α-oxide compound obtained by treating with alcoholic KOH. Cholesteryl acetate was reacted with NBS according to the Fieser's report. In this case two compounds, (C) and (D), corresponding to the above (A) and (B) were obtained, but the 6-one compound reported by Fieser could not be isolated.