Water → HCID 54498956, compound

HRID 918054Notes

Reaction equation

HRID 918054 reaction equation
[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>[Br:24][CH2:13][C:12](=[O:14])[C@@H:11]1[C@:15]2([CH3:23])[C@H:8]([C@H:7]3[C@H:18]([CH2:17][CH2:16]2)[C@:19]2([CH3:22])[C@H:4]([CH2:3][C@H:2]([OH:1])[CH2:21][CH2:20]2)[CH2:5][CH2:6]3)[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 92786Allopregnanolone

Product 1

HCID 54498956HCID 54498956, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A stirred solution of 3α-hydroxy-5α-pregnan-20-one (5 g., 15.7 mmole) in AR methanol (350 c.c.) was treated at 0° with a solution of bromine (1 c.c.) in methanol (23 c.c.) at such a rate that the yellow colour disappeared before further addition. The resultant suspension was poured into water and stirred for 30 minutes, and the precipitate was collected by filtration and dried in vacuo. The product was purified by column chromatography on silica gel MFC, (700 g.). Elution with benzene:ethyl acetate, 1:1) gave 21-bromo-3α-hydroxy-5α-pregnan-20-one (5.2 g.) [α]D + 105.5°.

Workup

  1. additiondisappeared before further addition
  2. filtrationthe precipitate was collected by filtration
  3. customdried in vacuo
  4. customThe product was purified by column chromatography on silica gel MFC, (700 g.)
  5. washElution with benzene

Sources & evidence

ORD record
ord-c35e207724a34d14a299f7dfd96408e5
Source dataset
uspto-grants-1976_07
Patent number
US03969345

Reaction notes

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