Sodium Hydroxide → HCID 86739910, compound

Participants

Reaction Steps

Methyl 11α-(2,2,2-trichloroethoxycarbonylamino)5α-androst-2-ene-17β-carboxylate (507 mg) in tetrahydrofuran (15 ml) and water (7.5 ml) was treated with N bromoacetamide (193 mg) and 60% perchloric acid (0.15 ml) and stirred at room temperature for 30 minutes. The reaction mixture was diluted with 5% sodium metabisulphite solution (30 ml) and water (50 ml). The suspension was extracted with ether (3×). The ether extracts were washed with water, dried and evaporated to give a foam. This was dissolved in methanol (50 ml), treated with 2M sodium hydroxide solution (10 ml), and stirred at room temperature for 30 minutes. The solution was concentrated by evaporation, diluted with water (100 ml) and extracted with ethyl acetate (3×). The extracts were washed with water (1×), dried and evaporated to give a white foam. This was purified by preparative t.l.c. in ethyl acetate/petrol (1:2) and crystallised from ether to give the title compound (90 mg) m.p. 153°-155° C., [α]D +25.2°.

Provenance & Evidence