11beta-Fluoro-7alpha-methylestr-4-ene-3,17-dione → 11beta-Fluoro-3-hydroxy-7alpha-methylestra-1,3,5(10)-trien-17-one

HRID 2215946Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2215946
[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C@@H:4]1[C:9]([CH2:10][C@H:11]2[CH3:21])=[CH:8][C:7](=[O:22])[CH2:6][CH2:5]1>C(#N)C.C(OCC)(=O)C.[Cu](Br)Br>[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][C:7]([OH:22])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH3:21]

Komponenten

5

Edukt 1

HCID 1019314411beta-Fluoro-7alpha-methylestr-4-ene-3,17-dione

Produkt 1

HCID 6720155211beta-Fluoro-3-hydroxy-7alpha-methylestra-1,3,5(10)-trien-17-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24611Copper bromide (CuBr2)KatalysatorHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

8.3 g (27.2 mmol) of 11β-fluoro-7α-methylestr-4-ene-3,17-dione in 260 ml of acetonitrile is mixed with 7.0 g (31.3 mmol) of copper(II) bromide, and the reaction mixture is stirred for 7 hours at room temperature. For working-up, the reaction solution is diluted with ethyl acetate, the organic phase is washed with aqueous ammonium chloride solution, sodium bicarbonate solution, and finally with water and dried on sodium sulfate. The crude product is chromatographed on silica gel (toluene-ethyl acetate, gradient of up to 7:3), yield 3.3 g (40%), [α]D+166.80 (c 0.5 methanol).

Aufarbeitung

  1. washthe organic phase is washed with aqueous ammonium chloride solution, sodium bicarbonate solution
  2. dry with materialfinally with water and dried on sodium sulfate
  3. customThe crude product is chromatographed on silica gel (toluene-ethyl acetate, gradient of up to 7:3), yield 3.3 g (40%), [α]D+166.80 (c 0.5 methanol)

Quellen und Nachweise

ORD-Eintrag
ord-f4a191802ce544be8a4e050340bc6a66
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109360B1

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