Through a mixture of 11 parts of charcoal containing 5% palladium and 2,000 parts of dioxane a stream of hydrogen is passed for 60 minutes. Then 86 parts of 17-ethynyl-19-nortestosterone (Norethindrone) in 1,500 parts of dioxane are added and the mixture is hydrogenated until 2 mols of hydrogen are absorbed. The catalyst is then removed by filtration and the solvent is
evaporated under vacuum. The crystalline residue is dissolved in 2,700 parts of benzene and thus applied to a chromatography column containing 5,000 parts of silica gel. The column is washed with 2,700 parts of benzene, 4,500 parts of a 10% solution of ethyl acetate in benzene and 27,000 parts of a 20% solution of ethyl acetate in benzene and is then eluted with 30,000 parts of a 30% solution of ethyl acetate in benzene. The resulting eluate is concentrated under vacuum and the residue is recrystallized from methanol and dried to constant weight at 75°C. The 17-ethyl-19-nortestosterone thus obtained melts at about 140°C to 141°C.
