Methanol → (S)-Methyl 2-(4-hydroxy-4-methylisoxazolidine-2-carbonyl)benzoate

HRID 270118Notes

Reaction equation

HRID 270118 reaction equation
Cl[CH2:2][C@@:3]([OH:18])([CH3:17])[CH2:4][O:5][N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:16].C(N(CC)CC)C.[CH3:26][OH:27]>>[CH3:26][O:27][C:7](=[O:16])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=1[C:14]([N:6]1[CH2:2][C@@:3]([OH:18])([CH3:17])[CH2:4][O:5]1)=[O:15]

Participants

4

Reactant 3

HCID 887MethanolHCID 8471TriethylamineHCID 689620112-[[(2R)-3-Chloro-2-hydroxy-2-methylpropyl]oxy]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 68958503(S)-Methyl 2-(4-hydroxy-4-methylisoxazolidine-2-carbonyl)benzoate

Procedure

A solution of 2-[[(2R)-3-Chloro-2-hydroxy-2-methylpropyl]oxy]-1H-isoindole-1,3 (2H)-dione (3.3 g, 12.2 mmol) in methanol (25 ml) was treated with triethylamine (3.4 ml) and heated under nitrogen at reflux for 1 h. The mixture was concentrated to dryness and purified by chromatography eluting with a gradient from dichloromethane to 5% methanol in dichloromethane. The chiral purity of the product was enhanced by recrystallising twice from acetonitrile to give the sub-title compound as a colourless solid (1.92 g).

Workup

  1. temperatureheated under nitrogen
  2. temperatureat reflux for 1 h
  3. concentrationThe mixture was concentrated to dryness
  4. custompurified by chromatography
  5. washeluting with a gradient from dichloromethane to 5% methanol in dichloromethane
  6. customby recrystallising twice from acetonitrile

Sources & evidence

ORD record
ord-bb818f784e554dca841c5a443796c33a
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

Loading…