Sodium Hydroxide → HCID 86739911, compound

Participants

Reaction Steps

Methyl 11α-(3-methylbutylamino)-5α-androst-2-ene-17β-carboxylate (403 mg) in tetrahydrofuran (15 ml), water (7 ml) and 2M hydrochloric acid (0.5 ml) was treated with N bromoacetamide (193 mg) and 60% perchloric acid (0.15 ml) and stirred for 30 min. 5% sodium metabisulphite (30 ml) was added and the resulting solution diluted with water and brought to pH 11 with 2M sodium hydroxide solution. This was extracted with ether and the ether extracts were washed with water, dried and evaporated to give an oil. This was dissolved in methanol (50 ml), treated with 2M sodium hydroxide (10 ml) and stirred for 30 min. The solution was concentrated by evaporation, diluted with water (100 ml) and extracted with ethyl acetate (3×). The extracts were washed with water, dried and evaporated to give an oil. This was purified by preparative t.l.c. in ethyl acetate to give the title compound (185 mg), [α]D +33.6°.

Provenance & Evidence