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

HRID 1606362Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1606362
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

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 thin layer chromatography and crystallisation from iso-propyl ether to give the title compound (70 mg.), m.p. 142°-146°, [α]D + 120.9°.

Aufarbeitung

  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 thin layer chromatography and crystallisation from iso-propyl ether

Quellen und Nachweise

ORD-Eintrag
ord-500f33fb88a943cfa58ddb73993b8f09
Quelldatensatz
uspto-grants-1976_04
Patentnummer
US03952031

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