Potassium Bicarbonate → 21-Hydroxy-5alpha-pregnane-3,11,20-trione

HRID 1576800Notes

Reaction equation

HRID 1576800 reaction equation
C([O:4][CH2:5][C:6](=[O:28])[C@@H:7]1[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@H:21]([C:22](=[O:26])[CH2:23]2)[C@:19]2([CH3:20])[C@H:14]([CH2:15][C:16](=[O:27])[CH2:17][CH2:18]2)[CH2:13][CH2:12]3)[CH2:9][CH2:8]1)(=O)C.C(=O)(O)[O-].[K+]>CO.O>[OH:4][CH2:5][C:6](=[O:28])[C@@H:7]1[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@H:21]([C:22](=[O:26])[CH2:23]2)[C@:19]2([CH3:20])[C@H:14]([CH2:15][C:16](=[O:27])[CH2:17][CH2:18]2)[CH2:13][CH2:12]3)[CH2:9][CH2:8]1

Participants

5

Reactant 2

HCID 516893Potassium BicarbonateHCID 7035596521-Acetoxy-5alpha-pregnane-3,11,20-trione

Product 1

HCID 7035523621-Hydroxy-5alpha-pregnane-3,11,20-trioneYield 71%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

21-Acetoxy-5α-pregnane-3,11,20-trione (4.85 g.) in hot methanol (200 ml.) was treated with potassium bicarbonate solution (10%; 20 ml.) and the stirred solution was refluxed under nitrogen for 15 minutes. The cooled reaction mixture was diluted with water and the oily precipitate was extracted into methylene chloride. The extract was washed with water, dried over sodium sulphate and evaporated to a foam (4.3 g.) which was triturated with ether to give title compound (3.07 g.) as white crystals, m.p. 164°-170°.

Workup

  1. temperaturethe stirred solution was refluxed under nitrogen for 15 minutes
  2. customThe cooled reaction mixture
  3. extractionthe oily precipitate was extracted into methylene chloride
  4. washThe extract was washed with water
  5. dry with materialdried over sodium sulphate
  6. customevaporated to a foam (4.3 g.) which
  7. customwas triturated with ether

Sources & evidence

ORD record
ord-ba0b2c621c4845f697c9ce468198cfc3
Source dataset
uspto-grants-1976_09
Patent number
US03983111

Reaction notes

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