Water → HCID 70191893, compound

Reaction equation

[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[CH2:27][C:26]2[CH:25]=[C:24]([OH:28])[CH:23]=[CH:22][C:21]=2[C@@H:20]2[C@@H:11]1[C@H:12]1[C@@:16]([CH2:18][CH2:19]2)([CH3:17])[C:15](=[O:29])[CH2:14][CH2:13]1)(=[O:3])[CH3:2].O.[BH4-].[Na+]>O1CCCC1>[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[CH2:27][C:26]2[CH:25]=[C:24]([OH:28])[CH:23]=[CH:22][C:21]=2[C@@H:20]2[C@@H:11]1[C@H:12]1[C@@:16]([CH2:18][CH2:19]2)([CH3:17])[C@@H:15]([OH:29])[CH2:14][CH2:13]1)(=[O:3])[CH3:2]

Participants

Procedure

6.0 g of 7α-(5-acetoxypentyl)-3-hydroxy-estra-1,3,5(10)-trien-17-one is dissolved in 65 ml of tetrahydrofuran, and 2 ml of water and 0.6 g of fine sodium borohydride are added at room temperature. After 1 hour of stirring at room temperature, the reaction mixture is added to ice water, extracted three times with ethyl acetate, and the organic phase is washed with sodium chloride solution, dried with sodium sulfate and concentrated by evaporation in a vacuum, raw yield 6.07 g.