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

HRID 2215946노트

반응식

HRID 2215946 반응식
[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]

참가 물질

5

반응물 1

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

생성물 1

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

시약·촉매·용매 3

HCID 24611Copper bromide (CuBr2)촉매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f4a191802ce544be8a4e050340bc6a66
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07109360B1

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