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

HRID 1606482노트

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HRID 1606482 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-8dd97b47fa164191b9ddef5a077ec623
출처 데이터셋
uspto-grants-1976_04
특허 번호
US03953429

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