Sodium Hydroxide → (3alpha,5alpha)-17-(3-Pyridinyl)androst-16-en-3-ol

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The method followed that described in Example 2, but using 3α-acetoxy-17-(3 -pyridyl)-5α-androst-16-ene (2.33 g, 5.9 mmol), methanol (40 ml), aqueous sodium hydroxide (10% w/v, 8 ml), and the mixture was heated at 80° C. for 20 min. Chromatography, on elution with toluene-methanol (40:1 ), afforded the title compound (1.62 g, 78%) which crystallised from toluene, m.p. 198°-199° C.; 1H-NMR(CDCl3) inter alia. δ0.84(3H,s,19-CH3), 1.00(3H,s,18-CH3), 4.06(1H,m,3β-H), 5.97(1H,m,16-H), 7.21(1H,m,Py 5-H), 7.64(1H,m,Py 4-H), 8.45(1H,m,Py 6-H), 8.61(1H,m,Py 2-H). Anal. Calcd: C, 82.00; H,9.46; N,3.99. Found: C,81.78; H,9.47; N.3.96%.

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