Water → HCID 68949346, compound

HRID 361672Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 10.34 g of lithium bromide and 53.2 g of copper(II) bromide in 280 ml of acetonitrile is added in drops to a solution of 47 g of 7α-(5-chloropentyl)-11β-fluoro-estr-4-ene-3,17-dione in 470 ml of acetonitrile at a bath temperature of 80° C. After 20 ml is added, the bleaching of the solution is awaited, and the remainder of the solution is added in 12 minutes and then stirred for 5 more minutes at a bath temperature of 80° C. Then, it is cooled to 0° C., mixed with sodium bicarbonate solution, added to water, extracted 4 times with ethyl acetate, washed neutral, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with hexane/ethyl acetate. 25.3 g of 7α-(5-chloropentyl)-11β-fluoro-3-hydroxy-estra-1,3,5(10)-trien-17-one is obtained. [α]D22 =+115.4°(c=0.5% in chloroform).

Workup

additionAfter 20 ml is added
additionthe remainder of the solution is added in 12 minutes
temperatureThen, it is cooled to 0° C.
extractionextracted 4 times with ethyl acetate
washwashed neutral
customdried on sodium sulfate
concentrationconcentrated by evaporation in a vacuum
customchromatographed on silica gel with hexane/ethyl acetate

Sources & evidence

ORD record: ord-42485cbbcf5d4f28aa3391d0acbc0753
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05866560

Reaction notes

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