Water → 17beta-Hydroxy-1alpha-methyl-5-alphaandrostan-3-one acetate

Participants

Reaction Steps

Variant 2 (in ethyl acetate : 66.1 g (0.2 mol) of 17β-acetoxy-androst-1-en-3-one is dissolved in 350 ml of dry ethyl acetate and mixed with 1.43 g (10 mmol) of copper(I) bromide. 188 ml (0.22 mol) of a 10% solution of trimethyl aluminum in toluene is added over 15 minutes to the reaction under nitrogen atmosphere, so that the temperature does not rise above 25° C. Then it is stirred for 30 minutes more. For hydrolysis, 15 ml of water is added to the reaction and stirred for 40 minutes more. The solid is suctioned off and absorptively precipitated three times, each with 200 ml of dioxane. After concentration by evaporation of the combined organic phases, 65.6 g of 17β-acetoxy-1α-methyl-androstan-3-one (95% of theory) of a melting point of 181° C. is obtained.

Provenance & Evidence