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

HRID 2215946Notes

Reaction equation

HRID 2215946 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-one

Reagents, catalysts & solvents 3

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

Procedure

8.3 g (27.2 mmol) of 11β-fluoro-7α-methylestr-4-ene-3,17-dione in 260 ml of acetonitrile is mixed with 7.0 g (31.3 mmol) of copper(II) bromide, and the reaction mixture is stirred for 7 hours at room temperature. For working-up, the reaction solution is diluted with ethyl acetate, the organic phase is washed with aqueous ammonium chloride solution, sodium bicarbonate solution, and finally with water and dried on sodium sulfate. The crude product is chromatographed on silica gel (toluene-ethyl acetate, gradient of up to 7:3), yield 3.3 g (40%), [α]D+166.80 (c 0.5 methanol).

Workup

  1. washthe organic phase is washed with aqueous ammonium chloride solution, sodium bicarbonate solution
  2. dry with materialfinally with water and dried on sodium sulfate
  3. customThe crude product is chromatographed on silica gel (toluene-ethyl acetate, gradient of up to 7:3), yield 3.3 g (40%), [α]D+166.80 (c 0.5 methanol)

Sources & evidence

ORD record
ord-f4a191802ce544be8a4e050340bc6a66
Source dataset
uspto-grants-2006_09
Patent number
US07109360B1

Reaction notes

Loading…