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

HRID 1838891Notes

Reaction equation

HRID 1838891 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-one

Reagents, catalysts & solvents 2

HCID 24611Copper bromide (CuBr2)CatalystHCID 6342AcetonitrileSolvent

Procedure

17.0 g of copper(II) bromide are added at 80° C. to 27.8 g of 7α-(5-bromopentyl)-11β-fluorooestr-4-ene-3,17-dione in 190 ml of acetonitrile. After 8 hours, the reaction mixture is stirred into water, extracted 3 times with ethyl acetate, washed twice with ammonium chloride, with sodium hydrogencarbonate and sodium chloride, dried and concentrated in vacuo. After chromatographing the crude product on silica gel using a hexane-ethyl acetate gradient, 20.4 g of 7α-(5-bromo-pentyl)-11β-fluoro-3-hydroxyestra-1,3,5(10)-trien-17-one are obtained as colourless crystals of melting point 178° C.

Workup

  1. extractionextracted 3 times with ethyl acetate
  2. washwashed twice with ammonium chloride, with sodium hydrogencarbonate and sodium chloride
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customare obtained as colourless crystals of melting point 178° C.

Sources & evidence

ORD record
ord-b83a279b3c5b4f2ba9ca0ef4fbeeed66
Source dataset
uspto-grants-2004_01
Patent number
US06677324B1

Reaction notes

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