Sodium borohydride → 7alpha-(6-Chlorohexyl)-11beta-fluor-estra-1,3,5(10)-triene-3,17-diol

HRID 1837244Notes

Reaction equation

HRID 1837244 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]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 158706707alpha-(6-Chlorohexyl)-11beta-fluor-3-hydroxy-estra-1,3,5(10)-trien-17-one

Product 1

HCID 699163977alpha-(6-Chlorohexyl)-11beta-fluor-estra-1,3,5(10)-triene-3,17-diolYield 97.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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.

Workup

  1. additionthe batch is added to saturated common salt solution
  2. extractionextracted with methylene chloride
  3. customdried on magnesium sulfate
  4. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-2e6239b428c2456d87a99d49f57b7d3e
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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