Hydrochloric Acid → Abiraterone

Participants

Reaction Conditions

Reaction Steps

To a solution of 3β-acetoxy-17-(3-pyridyl)androsta-5,16-diene (4.90 g, 12.5 mmol) in methanol (50 ml) was added an aqueous solution of sodium hydroxide (10% w/v, 10 ml) and the mixture heated, with stirring, on an oil bath at 80° C. for 5 min., then allowed to cool. The mixture was poured into water, neutralised with hydrochloric acid (1M), rebasified with saturated sodium bicarbonate solution, and extracted with hot toluene (3×100 ml). The toluene extracts were combined, dried (Na2CO3), and concentrated. Chromatography, on elution with toluene-diethyl ether (2:1) afforded the title compound (3.45 g, 79%) which crystallised from toluene, mp 228°-229° C.; 1H-NMR (CDCl3 inter alia δ1.05(3H,s,19-CH3), 1.07(3H,s,18-CH3), 3.54(1H,m,3α-H), (5.40H,dm,J 5.0 Hz, 6-H), 5.99(1H,m,16-H), 7.22(1H,m,Py5-H), 7.65(1H,m,Py 4-H), 8.46(1H,m,Py 6-H), 8.62(1H,m,Py 2-H). Anal. Calcd: C, 82.47; H, 8.94; N, 4.01. Found: C, 82.40; H, 8.91; N, 3.97%.

Provenance & Evidence