N-bromobutanimide → HCID 15380074, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 17β-Carbomethoxy-3,β,5α,6β-trihydroxy-androstane (43.5 g, 0.24 mol), as prepared in example 16, in 450 mL of dioxane is diluted with 50 mL of water, and maintained at 25° C. by means of an external cooling bath. To this suspension is added N-bromosuccinimide (22.5 g, 0.25 mol). The mixture is stirred for 8 h. The mixture is cooled in an ice bath and the solid collected by filtration, washed with 50% methanol/water, and air dried to afford 17β-carbomethoxy-6-oxo-3β,5α-dihydroxy-androstane as a white solid, mp 258°-260° C. Anal. Calcd. for C21H32O5 : C, 69.20; H, 8.85. Found: C, 69.38; H, 8.92.

Provenance & Evidence