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

HRID 2215946ノート

反応式

HRID 2215946 の反応式
[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]

参加物

5

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24611Copper bromide (CuBr2)触媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-f4a191802ce544be8a4e050340bc6a66
出典データセット
uspto-grants-2006_09
特許番号
US07109360B1

反応ノート

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