反应 #81459

反应方程式

diethyl(3-pyridyl)borane

androsta-3,5,16-trien-17-yl trifluoromethanesulphonate

sodium carbonate

→

title compound

收率 84.0%

17-(3-Pyridyl)androsta-3,5,16-triene

收率 84.0%

溶剂

THF

反应条件

后处理

1. 1
   洗涤Chromatography, on elution with dichloromethane

实验过程

The method followed that described in Example 1, using in step (b) diethyl(3-pyridyl)borane (0.88g, 6.0 mmol), androsta-3,5,16-trien-17-yl trifluoromethanesulphonate (2.01g, 5.0 mmol), prepared in step (a), THF (25 ml), bis(triphenylphosphine)palladium(II) chloride (35 mg, 0.05 mmol), and aqueous sodium carbonate (2M, 10 ml). Chromatography, on elution with dichloromethane, afforded the title compound (1.39 g, 84%) which crystallised from hexane, m.p. 110°-112° C. 1H-NMR (CDCl3) inter alia δ 1.02(3H,s,19-CH3), 1.07(3H,s,18-CH3), 5.44(1H,m,6-H), 5.61(1H,m,3-H), 5.95(1H,dm, J 9.8 Hz, 4-H), 6.01(1H,m, 16-H), 7.23(1H,m,Py 5-H), 7.66(1H,m,Py 4-H), 8.46(1H,m,Py 6-hr), 8.63(1H,m,Py 2-H); MS m/z 331 (M+).

来源