Water → 21-Bromo-3alpha-hydroxy-5beta-pregnan-20-one

HRID 650936

Reaktionsgleichung

Reaktionsgleichung von HRID 650936
[OH:1][C@@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:23])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1.[Br:24]Br.O>CO>[OH:1][C@@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:23])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH2:13][Br:24])[CH2:3]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 24408Bromine2×HCID 31402Pregnanolone

Produkt 1

HCID 8675425121-Bromo-3alpha-hydroxy-5beta-pregnan-20-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a flask containing a solution of 3α-hydroxy-5β-pregnan-20-one (5.15 g, 16.5 mmol) in methanol (100 mL) was added a solution of bromine (1.1 mL) in methanol (30 mL) dropwise in such a rate to maintain the brown color of the bromine until this color was persistent. Then water (200 mL) was added and the mixture was extracted with CH2Cl2 (3×100 mL). The combined extracts were dried over Na2SO4. Removal of the solvent resulted in the product as a foamy white solid (6.63 g). Other 21-bromo-pregnan-20-ones (3β-ethynyl-3α-hydroxy-21-bromo-5β-pregnan-20-one, 3β-methyl-3α-hydroxy-21-bromo-5α-pregnan-20-one and 3α-hydroxy-3β-trifluoromethyl-12-bromo-5β-19-norpregnan-20-one) were synthesized using the same method.

Aufarbeitung

  1. extractionthe mixture was extracted with CH2Cl2 (3×100 mL)
  2. dry with materialThe combined extracts were dried over Na2SO4
  3. customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-e294ab1d7c4b4f0fa17dac07a87cccb7
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06277838B1

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