Lithium Bromide → 7alpha-(5-Acetoxypentyl)-11-fluoro-3-hydroxyoestra-1,3,5(10)-trien-17-one

HRID 1838882Notes

Reaction equation

HRID 1838882 reaction equation
[Br-].[Li+].[C:3]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C@@H:12]1[CH2:29][C:28]2[C@H:23]([CH2:24][CH2:25][C:26](=[O:30])[CH:27]=2)[C@@H:22]2[C@@H:13]1[C@H:14]1[C@@:18]([CH2:20][C@@H:21]2[F:31])([CH3:19])[C:17](=[O:32])[CH2:16][CH2:15]1)(=[O:5])[CH3:4].C(=O)([O-])O.[Na+]>C(#N)C.[Cu](Br)Br>[C:3]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C@@H:12]1[CH2:29][C:28]2[CH:27]=[C:26]([OH:30])[CH:25]=[CH:24][C:23]=2[C@@H:22]2[C@@H:13]1[C@H:14]1[C@@:18]([CH2:20][CH:21]2[F:31])([CH3:19])[C:17](=[O:32])[CH2:16][CH2:15]1)(=[O:5])[CH3:4]

Participants

6

Reactant 3

HCID 82050Lithium BromideHCID 516892Sodium BicarbonateHCID 699353277alpha-(5-Acetoxypentyl)-11beta-fluorooestr-4-ene-3,17-dione

Product 1

HCID 699363457alpha-(5-Acetoxypentyl)-11-fluoro-3-hydroxyoestra-1,3,5(10)-trien-17-one

Reagents, catalysts & solvents 2

HCID 24611Copper bromide (CuBr2)CatalystHCID 6342AcetonitrileSolvent

Procedure

18.6 g of copper(II) bromide and 3.6 g of lithium bromide are added at 80° C. to 16.5 g of 7α-(5-acetoxy-pentyl)-11β-fluorooestr-4-ene-3,17-dione in 190 ml of acetonitrile. After 15 min, the reaction mixture is stirred into ice-water containing sodium hydrogen-carbonate. The precipitated product is filtered off with suction, dissolved in ethyl acetate, and the solution is washed with water, dried and concentrated in vacuo. After chromatographing the crude product on silica gel using a hexane-ethyl acetate gradient, 8.5 g of 7α-(5-acetoxypentyl)-11β-fluoro-3-hydroxyoestra-1,3,5(10)-trien-17-one are obtained as a foam.

Workup

  1. filtrationThe precipitated product is filtered off with suction
  2. dissolutiondissolved in ethyl acetate
  3. washthe solution is washed with water
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customare obtained as a foam

Sources & evidence

ORD record
ord-8ae82a424b16450cbba6cc34ef188bd0
Source dataset
uspto-grants-2004_01
Patent number
US06677324B1

Reaction notes

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