Potassium Carbonate → (6α)-17,21-Dihydroxy-6-Methylpregna-1,4,9(11)-triene-3,20-dione

HRID 1709159Notes

Reaction equation

HRID 1709159 reaction equation
C([O:4][CH2:5][C:6](=[O:29])[C@:7]1([OH:28])[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C:21](=[CH:22][CH2:23]2)[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:26])[CH:17]=[CH:18]2)[C@@H:13]([CH3:27])[CH2:12]3)[CH2:9][CH2:8]1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.O.C(OCC)(=O)C>[OH:28][C@:7]1([C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C:21](=[CH:22][CH2:23]2)[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:26])[CH:17]=[CH:18]2)[C@@H:13]([CH3:27])[CH2:12]3)[CH2:9][CH2:8]1)[C:6](=[O:29])[CH2:5][OH:4]

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 1506986693239-37-3

Product 1

HCID 15069867(6α)-17,21-Dihydroxy-6-Methylpregna-1,4,9(11)-triene-3,20-dione

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 13.58 g sample of 21-acetoxy-17α-hydroxy-6α-methylpregna-1,4,9-(11)-triene-3,20-dione in methanol (850 ml) was hydrolyzed with 10% potassium carbonate (34 ml). The reaction mixture was acidified, diluted with water and concentrated to give a gummy precipitate which was dissolved in ethyl acetate. The extract was washed with water and brine, then dried over sodium sulfate and evaporated. Crystallization of the residue from acetone-hexane gave the title compound Example 2(a), m.p. 204°-206° C.; one spot by TLC (10% CH3OH--CHCl3).

Workup

  1. concentrationconcentrated
  2. customto give a gummy precipitate which
  3. washThe extract was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customCrystallization of the residue from acetone-hexane

Sources & evidence

ORD record
ord-345831ff6825430e8f5b513a5dbcc271
Source dataset
uspto-grants-1990_08
Patent number
US04948533

Reaction notes

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