HCID 54243088, compound → HCID 13519094, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 533 mg of 10% Pd/C in 31 ml of cyclohexene and 46 ml of ethanol is stirred for one hour at 80° C. bath temperature. To this mixture is added 7.5 g of 17-acetoxy-1-chloromethyl-6-methylene-4-pregnene-3,20-dione and the mixture is further stirred for 18 hours at 80° C. Subsequently the catalyst is suctioned off, washed with warm ethanol, and the filtrate is combined with 7 ml of concentrated hydrochloric acid. The mixture is concentrated to one-third of the reaction volume and poured on an ice water-sodium chloride solution. After the usual working-up step, the crude product is purified on 700 g of silica gel with a hexane-ethyl acetate gradient. Yield: 4.3 g of 17α-acetoxy-6α-methyl-1α,2α-methylene-4-pregnene-3,20-dione, mp 198°-200° C.

Provenance & Evidence