Water → HCID 131710460, compound

HRID 1576795Notes

Reaction equation

HRID 1576795 reaction equation
[Br:1][C@H:2]1[CH2:21][C@@:20]2([CH3:22])[C@@H:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:19]2[C:18](=[O:23])[CH2:17][C@@:16]2([CH3:24])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[C:13](=[O:15])[CH3:14])[CH2:4][C@@H:3]1[OH:25].[Br:26]Br.O>CO>[Br:1][C@H:2]1[CH2:21][C@@:20]2([CH3:22])[C@@H:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:19]2[C:18](=[O:23])[CH2:17][C@@:16]2([CH3:24])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[C:13](=[O:15])[CH2:14][Br:26])[CH2:4][C@@H:3]1[OH:25]

Participants

5

Reactant 3

HCID 962WaterHCID 24408Bromine2×HCID 86733291HCID 86733291, compound

Product 1

HCID 131710460HCID 131710460, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of 2β-bromo-3α-hydroxy-5α-pregnane-11,20-dione (5.0 g.) in methanol (100 ml.) was treated at 0° with a solution of bromine (1 ml.) in methaol (30 ml.) at such a rate that the yellow colour disappeared before further addition of the bromine solution. The mixture was then poured into water and the precipitated solid was collected by filtration, washed with water and dried over P2O5 in vacuo. The resulting solid (5.0 g.) was purified by column chromatography (silica, EtOAc/ C6H6 1:2.5) to give crude 2β,21-dibromo-3α-hydroxy-5α-pregnane-11,20-dione (3,4 g.).

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washwashed with water
  3. dry with materialdried over P2O5 in vacuo
  4. customThe resulting solid (5.0 g.) was purified by column chromatography (silica, EtOAc/ C6H6 1:2.5)

Sources & evidence

ORD record
ord-98f0b5c75e4f487f993db9ec511dd17e
Source dataset
uspto-grants-1976_09
Patent number
US03983111

Reaction notes

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