Water → 11beta-Fluoro-7alpha-(5-bromopentyl)-3-hydroxy-estra-1,3,5(10)-trien-17-one

HRID 650368Notes

Reaction equation

HRID 650368 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:24][C:23]2[C@H:18]([CH2:19][CH2:20][C:21](=[O:25])[CH:22]=2)[C@@H:17]2[C@@H:8]1[C@H:9]1[C@@:13]([CH2:15][C@@H:16]2[F:26])([CH3:14])[C:12](=[O:27])[CH2:11][CH2:10]1.O>C(#N)C.[Cu](Br)Br>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:24][C:23]2[CH:22]=[C:21]([OH:25])[CH:20]=[CH:19][C:18]=2[C@@H:17]2[C@@H:8]1[C@H:9]1[C@@:13]([CH2:15][C@@H:16]2[F:26])([CH3:14])[C:12](=[O:27])[CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 962WaterHCID 158706627alpha-(5-Bromopentyl)-11beta-fluoro-estr-4-ene-3,17-dione

Product 1

HCID 1587066311beta-Fluoro-7alpha-(5-bromopentyl)-3-hydroxy-estra-1,3,5(10)-trien-17-oneYield 73.7%

Reagents, catalysts & solvents 2

HCID 24611Copper bromide (CuBr2)CatalystHCID 6342AcetonitrileSolvent

Procedure

17.0 g of copper(II) bromide is added to 27.8 g of 7α-(5-bromopentyl)-11β-fluoro-estr-4-ene-3,17-dione in 190 ml of acetonitrile at 80° C. After 8 hours, the reaction mixture is stirred into water, extracted three times with ethyl acetate, washed twice with ammonium chloride, with sodium bicarbonate and common salt, dried and concentrated by evaporation in a vacuum. After the crude product is chromatographed on silica gel with a hexane-ethyl acetate gradient, 20.4 g of 7α-(5-bromopentyl)-11β-fluoro-3-hydroxy-estra-1,3,5(10)trien-17-one is obtained as colorless crystals with a melting point of 178° C.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washwashed twice with ammonium chloride, with sodium bicarbonate and common salt
  3. customdried
  4. concentrationconcentrated by evaporation in a vacuum
  5. customAfter the crude product is chromatographed on silica gel with a hexane-ethyl acetate gradient

Sources & evidence

ORD record
ord-8db5b0523d4743e6ad2be874f9c9c162
Source dataset
uspto-grants-2001_08
Patent number
US06271403B1

Reaction notes

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