Hydrochloric Acid → 7alpha-(6-Chlorohexyl)-11beta-fluor-3-hydroxy-estra-1,3,5(10)-trien-17-one

HRID 650372Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

28.1 g of copper(II) bromide and 5.4 g of lithium bromide in 105 ml of anhydrous acetonitrile are added to 25.2 g of 7α-(6-chlorohexyl)-11β-fluoro-estr-4-ene-3,17-dione in 175 ml of anhydrous acetonitrile at 80° C. After 15 minutes, the reaction mixture is cooled to 0° C., and 250 ml of saturated sodium bicarbonate solution is added in drops. Then, the solution is stirred into 1 liter of water, brought to pH=6 with 2N hydrochloric acid, extracted 3 times with ethyl acetate, washed with common salt solution, dried on magnesium sulfate and concentrated by evaporation in a vacuum. Chromatography of the crude product on silica gel with a hexane-ethyl acetate gradient yields 5.7 g of 7α-(6-chlorohexyl)-11β-fluoro-3-hydroxy-estra-1,3,5(10)-trien-17-one as a foam.

Workup

extractionextracted 3 times with ethyl acetate
washwashed with common salt solution
customdried on magnesium sulfate
concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record: ord-d68f4500db584a32a1f92f8ba8379188
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06271403B1

Reaction notes

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