Sodium Carbonate → 3alpha-Acetoxy-17-(3-pyridyl)-5alpha-androst-16-ene

Beteiligte Stoffe

Reaktionsschritte

The method followed that described in Example 1, using in step (b) diethyl(3-pyridyl)borane (1.41 g, 9.6 mmol), 3α-acetoxy-5α-androst-16-en-17-yl trifluoromethanesulphonate (3.44 g, 7.4 mmol), prepared from the 3α-acetoxy-5α-androstan-17-one by the method of step (a), THF (40 ml), bis(triphenylphosphine)palladium(II) chloride (52 mg, 0.07 mmol), and aqueous sodium carbonate (2M, 15 mmol). Chromatography, on elution with light petroleum-diethyl ether (2:1), afforded the title compound (2.39 g, 82%), 1H-NMR (CDCl3) inter alia δ0.85(3H,s, 19-CH3), 1.01(3H,s,18-CH3), 2.06(3H,s,CH3CO2), 5.02(1H,m,3β-H), 6.00(1H,m,16-H), 7.24(1H,m,Py 5-H), 7.68(1H,m,Py 4-H), 8.47(1H,m,Py 6-H), 8.63(1H,m,Py 2-H); MS m/z 393 (M+).

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