Water → (2beta,3alpha,5alpha)-21-(Acetyloxy)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnan-20-one

HRID 233509Notes

Reaction equation

HRID 233509 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[K+].[OH:6][C@@H:7]1[C@@H:31]([N:32]2[CH2:37][CH2:36][O:35][C:34]([CH3:39])([CH3:38])[CH2:33]2)[CH2:30][C@@:29]2([CH3:40])[C@@H:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:28]2[CH2:27][CH2:26][C@@:25]2([CH3:41])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C:17](=[O:24])[CH2:18]OS(C)(=O)=O)[CH2:8]1.O>C(O)C>[C:1]([O:4][CH2:18][C:17](=[O:24])[C@@H:16]1[C@:25]2([CH3:41])[C@H:13]([C@H:12]3[C@H:28]([CH2:27][CH2:26]2)[C@:29]2([CH3:40])[C@H:9]([CH2:8][C@H:7]([OH:6])[C@@H:31]([N:32]4[CH2:37][CH2:36][O:35][C:34]([CH3:39])([CH3:38])[CH2:33]4)[CH2:30]2)[CH2:10][CH2:11]3)[CH2:14][CH2:15]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 517044Potassium AcetateHCID 10673665HCID 10673665, compound

Product 1

HCID 10577010(2beta,3alpha,5alpha)-21-(Acetyloxy)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnan-20-oneYield 35.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Anhydrous potassium acetate (470 mg) was added to (2β,3α,5α)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)-21-[(methylsulfonyl)oxy]pregnan-20-one (1.0 g) in ethanol (15 ml) and the solution was heated under reflux for 1.5 h. The reaction mixture was poured into water (150 ml) and the precipitated solid was filtered off, washed with water and the solid was dissolved in dichloromethane. After drying the solution over sodium sulfate, the solvent was removed under reduced pressure and the residue was chromatographed on silica gel. The purified product was crystallised from methanol to give (2β,3α,5α)-21-(acetyloxy)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnan-20-one (330 mg). m.p. 174°-175° C.; [α]D +13.9° (c 0.5).

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 1.5 h
  3. filtrationthe precipitated solid was filtered off
  4. washwashed with water
  5. dissolutionthe solid was dissolved in dichloromethane
  6. dry with materialAfter drying the solution over sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customthe residue was chromatographed on silica gel
  9. customThe purified product was crystallised from methanol

Sources & evidence

ORD record
ord-5917f1fd612d454ea1088ee8daca277b
Source dataset
uspto-grants-1997_01
Patent number
US05593983

Reaction notes

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