Pyrrolidone carboxylic acid → Methyl 5-oxo-DL-prolinate

HRID 2194358Notes

Reaction equation

HRID 2194358 reaction equation
[O:1]=[C:2]1[NH:6][CH:5]([C:7]([OH:9])=[O:8])[CH2:4][CH2:3]1.[CH3:10]O>>[CH3:10][O:8][C:7]([CH:5]1[CH2:4][CH2:3][C:2](=[O:1])[NH:6]1)=[O:9]

Participants

3

Reactant 2

HCID 499Pyrrolidone carboxylic acidHCID 887Methanol

Product 1

HCID 500249Methyl 5-oxo-DL-prolinateYield 90%

Procedure

A mixture of 5-oxo-pyrrolidine-2-carboxylic acid (5 g, 38.7 mmol) and Amberlyst® 15 (5 g) in MeOH (50 ml) was refluxed for 20 hours. After cooling, the reaction was filtered and the solvent removed under vacuum to afford the title compound (4.9 g, 90% yield) that was used without further purification in the next step.

Workup

  1. temperaturewas refluxed for 20 hours
  2. temperatureAfter cooling
  3. filtrationthe reaction was filtered
  4. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-354411542cd84f948f6d9dfc21503b48
Source dataset
uspto-grants-2012_12
Patent number
US08334286B2

Reaction notes

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