Reacción #448841

ord-dc6266e3a7e249018ce85d749429f96d

Ecuación de reacción

[Br-].[Li+]
lithium bromide
CC(=O)OCCCCC[C@@H]1CC2=CC(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CCC(=O)[C@@]1(C)C[C@@H]2F
7α-(5-acetoxypentyl)-11β-fluoro-estr-4-ene-3,17-dione
O=C([O-])O.[Na+]
sodium bicarbonate
→
CC(=O)OCCCCC[C@@H]1Cc2cc(O)ccc2[C@@H]2[C@@H]1[C@@H]1CCC(=O)[C@@]1(C)C[C@@H]2F
7α-(5-acetoxypentyl)-11β-fluoro-3-hydroxy-estra-1,3,5(10)-trien-17-one
Rendimiento 51.8%

Reactantes

—
ice water
[Br-].[Li+]
lithium bromide
CC(=O)OCCCCC[C@@H]1CC2=CC(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CCC(=O)[C@@]1(C)C[C@@H]2F
7α-(5-acetoxypentyl)-11β-fluoro-estr-4-ene-3,17-dione
O=C([O-])O.[Na+]
sodium bicarbonate

Reactivos

[Br][Cu][Br]
copper(II) bromide

Disolventes

CCOC(C)=O
ethyl acetate
CC#N
acetonitrile

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Lavadowashed with water
  2. 2
    Otrodried
  3. 3
    Concentraciónconcentrated by evaporation in a vacuum
  4. 4
    OtroAfter the crude product is chromatographed on silica gel with a hexane-ethyl acetate gradient

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05866560uspto-grants-1999_02