[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH2:9][C:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C:12](=[O:20])[CH:11]=4)[C@@H:6]1[CH2:5][CH2:4][CH2:3]2.[OH:21]O.[OH-].[Na+]>CO.O>[O:21]1[C:10]23[C@:15]([CH3:16])([CH2:14][CH2:13][C:12](=[O:20])[C@H:11]12)[C@@H:17]1[C@H:7]([C@H:6]2[C@@:2]([CH2:19][CH2:18]1)([CH3:1])[CH2:3][CH2:4][CH2:5]2)[CH2:8][CH2:9]34-Androstene-3-one (4.3g) is dissolved in 300ml of methanol and cooled to 3° C in an ice-water bath. To the cooled mixture is added 20ml of 30% hydrogen peroxide and 26ml of 4N sodium hydroxide solution simultaneously from 2 dropping funnels. The addition is carried out in a nitrogen atmosphere with stirring. The mixture is allowed to warm to room temperature and stirring is continued for an additional hour. The mixture is diluted with 4 liters of water and extracted with methylene chloride. The organic layer is dried over sodium sulfate and concentrated to yield 3.0g of the title compound.
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