17-Cyclopropyloxy-4-nitroandrost-4-en-3-one → 4-Amino-17-cyclopropyloxyandrost-4-en-3-one

Participants

Reaction Steps

A solution of 17-cyclopropyloxy-4-nitroandrost-4-en-3-one (1.0 g, 2.71 mM) in acetic acid (10 mL) is treated with zinc dust (1.0 g). The combination is vigorously stirred for 1.5 hours at room temperature. The zinc salts are removed by filtration and washed with ethyl acetate. The combined filtrate and wash are combined and concentrated to a yellow solid which is then redissolved in ethyl acetate and extracted three times with 1M hydrochloric acid (150 ml). The combined acid extracts are neutralized with sodium hydroxide (pH 14) and further extracted with ether. The combined organic layers are then dried over sodium sulfate and concentrated to give 4-amino-17-cyclopropyloxyandrost-4-en-3-one (0.59 g), m.p. 100°-102° C. (aqueous methanol). IR 3354, 1662, 1620, 1581 cm-1MS(CI) 344(100%, M+1) 1H-NMR 0.37-0.61(4H, m, 2 x cyclopropyl CH2), 0.79(3H, s, C18 -Me), 1.16(s, Ci9 -Me), 3.25-3.33(m, cyclopropyl-CHO), 3.44(t, C17 -H).

Provenance & Evidence