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

HRID 650348Notes

Reaction equation

HRID 650348 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.C(OCC)(=O)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][C@@H:21]2[F:31])([CH3:19])[C:17](=[O:32])[CH2:16][CH2:15]1)(=[O:5])[CH3:4]

Participants

7

Reactant 3

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

Product 1

HCID 699351197alpha-(5-Acetoxypentyl)-11beta-fluoro-3-hydroxy-estra-1,3,5(10)-trien-17-oneYield 51.8%

Reagents, catalysts & solvents 3

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

Procedure

18.6 of copper(II) bromide and 3.6 g of lithium bromide are added to 16.5 g of 7α-(5-acetoxypentyl)-11β-fluoro-estr-4-ene-3,17-dione in 190 ml of acetonitrile at 80° C. After 15 minutes, the reaction mixture is stirred into sodium bicarbonate-containing ice water. The precipitated product is suctioned off, dissolved in ethyl acetate, washed with water, dried and concentrated by evaporation in a vacuum. After the crude product is chromatographed on silica gel with a hexane-ethyl acetate gradient, 8.5 g of 7α-(5-acetoxypentyl)-11β-fluoro-3-hydroxy-estra-1,3,5(10)-trien-17-one is obtained as foam.

Workup

  1. washwashed with water
  2. customdried
  3. concentrationconcentrated by evaporation in a vacuum
  4. customAfter the crude product is chromatographed on silica gel with a hexane-ethyl acetate gradient

Sources & evidence

ORD record
ord-ba74732a6bca414eb3cdeed3be18a116
Source dataset
uspto-grants-2001_08
Patent number
US06271403B1

Reaction notes

Loading…