Water → 21-Bromo-3alpha-hydroxy-2beta-methoxy-5alpha-pregnan-20-one

HRID 1077022Notes

Reaction equation

HRID 1077022 reaction equation
[OH:1][C@@H:2]1[C@@H:21]([O:22][CH3:23])[CH2:20][C@@:19]2([CH3:24])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:25])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1.[Br:26]Br.O>CO>[Br:26][CH2:13][C:12](=[O:14])[C@@H:11]1[C@:15]2([CH3:25])[C@H:8]([C@H:7]3[C@H:18]([CH2:17][CH2:16]2)[C@:19]2([CH3:24])[C@H:4]([CH2:3][C@H:2]([OH:1])[C@@H:21]([O:22][CH3:23])[CH2:20]2)[CH2:5][CH2:6]3)[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 700865362beta-Methoxy-3alpha-hydroxy-5alpha-pregnan-20-one

Product 1

HCID 12129189121-Bromo-3alpha-hydroxy-2beta-methoxy-5alpha-pregnan-20-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A stirred solution of 3α-hydroxy-2β-methoxy-5α-pregnan-20-one (4.0 g.) in dry methanol (300 ml.) was treated at 0° with a solution of bromine (0.65 ml.) in methanol (15 ml.) at such a rate that the yellow colour disappeared before further addition. The mixture was then poured into water and the precipitated solid was collected by filtration, washed with water and dried in vacuo to give title compound (4.0 g) as white crystals.

Workup

  1. additiondisappeared before further addition
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-3084ffaff1084e35b35bd080e2c5fa50
Source dataset
uspto-grants-1976_05
Patent number
US03959260

Reaction notes

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