Water → 4-Androstene-3,17-dione, 1alpha-methyl-

Participants

Reaction Conditions

Reaction Steps

14.2 g (50 mmol) of androsta-1,4-diene-3,17-dione is dissolved under nitrogen atmosphere in 100 ml of anhydrous dioxane. 716 mg (5 mmol) of copper(I) bromide is added and the solution is heated to 25° C. Then, 47 ml (55 mmol) of a 10% trimethylaluminum solution in toluene is added to the reaction, so that the temperature does not rise above 35° C. Then, it is stirred for 1.5 more hours at 35° C. For hydrolysis, 2.5 ml of water mixed with 10 ml of dioxane is added to the reaction and the solution is stirred for 15 more minutes. The inorganic solid is suctioned off and rewashed with 30 ml of dioxane. After concentration by evaporation of the dioxane solution, 17 g of crude product is obtained, which is chromatographed as eluent on silica gel with hexane/ethyl acetate mixtures. After concentration by evaporation of the fractions and recrystallization from diisopropyl ether, 11.66 g of 1α-methylandrost-4-ene-3,17-dione (77% of theory) of melting point 154° C. is obtained.

Provenance & Evidence