Water → 3alpha-Acetoxy-2beta-bromo-5alpha-pregnan-20-one

HRID 1606482ノート

反応式

HRID 1606482 の反応式
[OH:1][C@@H:2]1[C@@H:21]([Br:22])[CH2:20][C@@:19]2([CH3:23])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:24])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1.[C:25](OC(=O)C)(=[O:27])[CH3:26].O>N1C=CC=CC=1>[C:25]([O:1][C@@H:2]1[C@@H:21]([Br:22])[CH2:20][C@@:19]2([CH3:23])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:24])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1)(=[O:27])[CH3:26]

参加物

5

反応物 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 572036952beta-Bromo-3alpha-hydroxy-5alpha-pregnan-20-one

生成物 1

HCID 867332963alpha-Acetoxy-2beta-bromo-5alpha-pregnan-20-one

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A solution of 3α-hydroxy-2β-bromo-5α-pregnan-20-one (8.5 g.) in pyridine (25 ml.) was treated with acetic anhydride (12.5 ml.), and the mixture was allowed to stand at room temperature overnight. The reaction mixture was poured into water and the product was extracted with methylene chloride. The extract was washed with water, dried (Na2SO4) and evaporated. A portion (582 mg.) of the residue (8.5 g.) was purified by preparative t.l.c. and crystallisation from iso-propyl ether to give 3α-acetoxy-2β-bromo-5α-pregnan-20-one (70 mg.), 142°-146°, [α]D + 120.9°.

後処理

  1. extractionthe product was extracted with methylene chloride
  2. washThe extract was washed with water
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customA portion (582 mg.) of the residue (8.5 g.) was purified by preparative t.l.c
  6. customand crystallisation from iso-propyl ether

出典と根拠

ORDレコード
ord-8dd97b47fa164191b9ddef5a077ec623
出典データセット
uspto-grants-1976_04
特許番号
US03953429

反応ノート

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