HCID 10193144, compound → 11beta-Fluoro-3-hydroxy-7alpha-methylestra-1,3,5(10)-trien-17-one

HRID 855484Notes

Reaction equation

HRID 855484 reaction equation
[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C@@H:4]1[C:9]([CH2:10][C@H:11]2[CH3:21])=[CH:8][C:7](=[O:22])[CH2:6][CH2:5]1>C(#N)C.C(OCC)(=O)C.[Cu](Br)Br>[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][C:7]([OH:22])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH3:21]

Participants

5

Reactant 1

HCID 10193144HCID 10193144, compound

Product 1

HCID 6720155211beta-Fluoro-3-hydroxy-7alpha-methylestra-1,3,5(10)-trien-17-oneYield 56.4%

Reagents, catalysts & solvents 3

HCID 24611Copper bromide (CuBr2)CatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 500 mg of 11β-fluoro-7α-methylestr-4-ene-3,17-dione in 16.5 ml of acetonitrile was stirred with 400 mg of copper(II) bromide for 6.5 hours at 25° C. Then, it was diluted with ethyl acetate, washed with sodium bicarbonate solution and sodium chloride solution, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with hexane/acetone. 280 mg of pure 11β-fluoro-3-hydroxy-7α-methylestra-1,3,5(10)-trien-17-one with a melting point of 185-186° C. was obtained.

Workup

  1. washwashed with sodium bicarbonate solution and sodium chloride solution
  2. customdried on sodium sulfate
  3. concentrationconcentrated by evaporation in a vacuum
  4. customchromatographed on silica gel with hexane/acetone

Sources & evidence

ORD record
ord-7c5e1167d2744fa0ad35afc2048b0ffb
Source dataset
uspto-grants-2007_08
Patent number
US07262023B2

Reaction notes

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