Water → HCID 70191893, compound

HRID 1595968Notes

Reaction equation

HRID 1595968 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

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 158381587alpha-(5-Acetoxypentyl)-3-hydroxy-estra-1,3,5(10)-trien-17-one

Product 1

HCID 70191893HCID 70191893, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washthe organic phase is washed with sodium chloride solution
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-dc9a94fbb8394536ba76a00f53d01300
Source dataset
uspto-grants-2001_09
Patent number
US06288051B1

Reaction notes

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