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Water → 11beta-Fluoro-7alpha-(5-bromopentyl)-3-hydroxy-estra-1,3,5(10)-trien-17-one

HRID 1837209
ノート
印刷プレビュー

反応式

HRID 1837209 の反応式
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:24][C:23]2[C@H:18]([CH2:19][CH2:20][C:21](=[O:25])[CH:22]=2)[C@@H:17]2[C@@H:8]1[C@H:9]1[C@@:13]([CH2:15][C@@H:16]2[F:26])([CH3:14])[C:12](=[O:27])[CH2:11][CH2:10]1.O>C(#N)C.[Cu](Br)Br>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:24][C:23]2[CH:22]=[C:21]([OH:25])[CH:20]=[CH:19][C:18]=2[C@@H:17]2[C@@H:8]1[C@H:9]1[C@@:13]([CH2:15][C@@H:16]2[F:26])([CH3:14])[C:12](=[O:27])[CH2:11][CH2:10]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 962WaterHCID 158706627alpha-(5-Bromopentyl)-11beta-fluoro-estr-4-ene-3,17-dione

生成物 1

HCID 1587066311beta-Fluoro-7alpha-(5-bromopentyl)-3-hydroxy-estra-1,3,5(10)-trien-17-one収率 73.7%

試薬・触媒・溶媒 2

HCID 24611Copper bromide (CuBr2)触媒HCID 6342Acetonitrile溶媒

実験手順

17.0 g of copper(II) bromide is added to 27.8 g of 7α-(5-bromopentyl)-11β-fluor-estr-4-ene-3,17-dione in 190 ml of acetonitrile at 80° C. After 8 hours, the reaction mixture is stirred into water, extracted three times with ethyl acetate, and twice with ammonium chloride, washed with sodium bicarbonate and common salt, dried and concentrated by evaporation in a vacuum. After the crude product is chromatographed on silica gel with a hexane-ethyl acetate gradient, 20.4 g of 7α-(5-bromopentyl)-11β-fluoro-3-hydroxy-estra-1,3,5(10)-trien-17-one is obtained as colorless crystals with a melting point of 178° C.

後処理

  1. extractionextracted three times with ethyl acetate
  2. washtwice with ammonium chloride, washed with sodium bicarbonate and common salt
  3. customdried
  4. concentrationconcentrated by evaporation in a vacuum
  5. customAfter the crude product is chromatographed on silica gel with a hexane-ethyl acetate gradient

出典と根拠

ORDレコード
ord-e0551b11c1d8422e978226ad08329f43
出典データセット
uspto-grants-2004_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06780855B2

反応ノート

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