4,5-Dihydro-5-(methoxycarbonyl)-3-isoxazolepropanoic acid methyl ester → 5-Oxo-alpha-hydroxy-2-pyrrolidinepropanoic acid methyl ester

HRID 653412Notes

Reaction equation

HRID 653412 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]1[CH2:10][CH:9]([C:11]([O:13][CH3:14])=[O:12])[O:8][N:7]=1>CO.O=[Pt]=O>[CH3:14][O:13][C:11](=[O:12])[CH:9]([OH:8])[CH2:10][CH:6]1[CH2:5][CH2:4][C:3](=[O:2])[NH:7]1

Participants

4

Reactant 1

HCID 139115534,5-Dihydro-5-(methoxycarbonyl)-3-isoxazolepropanoic acid methyl ester

Product 1

HCID 139115545-Oxo-alpha-hydroxy-2-pyrrolidinepropanoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A suspension of 40 g of 4,5-dihydro-5-methoxycarbonyl-3-isoxazolepropanoic acid methyl ester and 2.0 g of PtO2 in 400 ml of methanol is placed under a hydrogen atmosphere with agitation. After H2 absorption is complete, the solution is filtered and the solvent removed under reduced pressure to give an oil. The oil is triturated with anhydrous diethyl ether to yield 5-oxo-alpha-hydroxy-2-pyrrolidinepropanoic acid methyl ester as a white solid with mp 87°-90° C. NMR (CDCl3) and 6.94 (s, 1H), 4.38 (m, 1H), 3.96 (d, 1H), 3.73 (m, 1H), 3.70 (s, 3H), 2.44-1.81 (m, 6H). Ir(KBr) 3330, 3200, 2980, 1734, 1696, 1436, 1416, 1400, 1382, 1362, 1313, 1297, 1246, 1212.

Workup

  1. customAfter H2 absorption
  2. filtrationthe solution is filtered
  3. customthe solvent removed under reduced pressure
  4. customto give an oil
  5. customThe oil is triturated with anhydrous diethyl ether

Sources & evidence

ORD record
ord-5d243b4302bd446aa8e4501ec53a1ce5
Source dataset
uspto-grants-1987_06
Patent number
US04677114

Reaction notes

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