Sodium borohydride → 7alpha-(6-Chlorohexyl)-11beta-fluor-estra-1,3,5(10)-triene-3,17-diol
Reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C@@H:8]1[CH2:25][C:24]2[CH:23]=[C:22]([OH:26])[CH:21]=[CH:20][C:19]=2[C@@H:18]2[C@@H:9]1[C@H:10]1[C@@:14]([CH2:16][C@@H:17]2[F:27])([CH3:15])[C:13](=[O:28])[CH2:12][CH2:11]1.[BH4-].[Na+]>CO>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C@@H:8]1[CH2:25][C:24]2[CH:23]=[C:22]([OH:26])[CH:21]=[CH:20][C:19]=2[C@@H:18]2[C@@H:9]1[C@H:10]1[C@@:14]([CH2:16][C@@H:17]2[F:27])([CH3:15])[CH:13]([OH:28])[CH2:12][CH2:11]1Participants
4
Procedure
611 mg of 7α-(6-chlorohexyl)-11β-fluor-3-hydroxy-estra-1,3,5(10)-trien-17-one is dissolved in 10 ml of methanol and carefully mixed with 166 mg of sodium borohydride. After 15 minutes of stirring at room temperature, the batch is added to saturated common salt solution, extracted with methylene chloride, dried on magnesium sulfate and concentrated by evaporation in a vacuum. 599 mg of 7α-(6-chlorohexyl)-11β-fluor-estra-1,3,5(10)-triene-3,17-diol is obtained as a crude product, which is used without further purification in the next stage.