HCID 70501729, compound → HCID 70501193, compound

Participants

Reaction Conditions

Reaction Steps

Jones reagent (21.0 ml; 8N) was added dropwise to a stirred suspension of 16β-(1-piperidinyl)-5α-androstane-2β,17β-diol 17-acetate (14.0 g) in acetone (250 ml), cooled to approx. 5° C. in an ice-bath. When the addition was complete, the cooling bath was removed and stirring was continued for 3 h. Saturated sodium carbonate solution (100 ml) was added to give pH approx. 9 and the product was extracted into dichloromethane (150 ml). The organic layer was separated, washed neutral with water (3×150 ml) and dried (MgSO4). The solution was concentrated while ether was added to afford 17β-acetyloxy-16β-(1-piperidinyl)-5α-androstan-2-one (12.2 g) m.p. 165°-167° C.; [α]D +44.6° (c 0.45 in CHCl3).

Provenance & Evidence