[C:1]([OH:4])(=O)[CH3:2].CC(C)=[O:7].[CH3:9][C@:10]12[CH2:27][CH2:26][C@H:25]3[C@@H:15]([CH2:16][CH2:17][CH:18]4[C@:23]3([CH3:24])[CH2:22]CC[CH2:19]4)[C@@H:14]1[CH2:13][CH2:12][C:11]2=[O:28]>C(Cl)(Cl)Cl.[Pt]=O>[OH:4][C@H:1]1[CH2:2][CH2:24][C@@:23]2([CH3:22])[CH:18]([CH2:17][CH2:16][C@@H:15]3[C@@H:25]2[CH2:26][CH2:27][C@@:10]2([CH3:9])[C@:14]3([OH:7])[CH2:13][CH2:12][C:11]2=[O:28])[CH2:19]1The hydrogenation of 14β-hydroxy-9(11)-androsten-3,17-dione (100 mg.) was carried out over 50 mg. of platinum oxide in 25 ml. of glacial acetic acid. When consumption of hydrogen had ceased, the catalyst was filtered, the solvent was evaporated under vacuum and the product was isolated by chromatography on silica gel using a mixture of 10% acetone in chloroform to afford 70 mg. (~70%) of the androstan-17-one, m.p. 214°-217°.
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