Water → 3beta-Hydroxy-5beta-androstan-17-one

HRID 1438959Notes

Reaction equation

HRID 1438959 reaction equation
[OH-].[Na+].O.C([O:7][C@H:8]1[CH2:25][CH2:24][C@@:23]2([CH3:26])[C@H:10]([CH2:11][CH2:12][C@@H:13]3[C@@H:22]2[CH2:21][CH2:20][C@@:18]2([CH3:19])[C@H:14]3[CH2:15][CH2:16][C:17]2=[O:27])[CH2:9]1)(=O)C>CO>[OH:7][C@H:8]1[CH2:25][CH2:24][C@@:23]2([CH3:26])[C@H:10]([CH2:11][CH2:12][C@@H:13]3[C@@H:22]2[CH2:21][CH2:20][C@@:18]2([CH3:19])[C@H:14]3[CH2:15][CH2:16][C:17]2=[O:27])[CH2:9]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 68119340HCID 68119340, compound

Product 1

HCID 2477323beta-Hydroxy-5beta-androstan-17-oneYield 98.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 7.6 parts of sodium hydroxide in 25 parts of water is added to a solution of 42.5 parts of 3β-acetoxy-5β-androstan-17-one in 140 parts of methanol with stirring. The resultant mixture is heated to reflux for 2 hours whereupon distillation is initiated and 109 parts of methanol are removed. The remaining methanol is removed by evaporation and the resulting crystalline solid is diluted with water and stirred. The crystals are collected by filtration, washed with water until the washings are about pH 6 and air-dried to afford, in 98.5% yield, 3β-hydroxy-5β-androstan-17-one. This compound melts at about 152°-155° C. and exhibits infrared absorption maxima in chloroform at 3620, 2940, 1735 cm-1 and is represented by the following structural formula. ##STR5##

Workup

  1. temperatureto reflux for 2 hours whereupon distillation
  2. custom109 parts of methanol are removed
  3. customThe remaining methanol is removed by evaporation
  4. additionthe resulting crystalline solid is diluted with water
  5. stirringstirred
  6. filtrationThe crystals are collected by filtration
  7. washwashed with water until the washings
  8. customair-dried

Sources & evidence

ORD record
ord-684cdeb6bc5344e59600d8bae8cb44de
Source dataset
uspto-grants-1977_11
Patent number
US04057543

Reaction notes

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