Itaconic acid → 1-(2,4-Dimethoxybenzyl)-5-oxopyrrolidine-3-carboxylic acid

HRID 58888

Reaction equation

HRID 58888 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]([CH2:4][C:5]([OH:7])=O)=[CH2:3].[CH3:10][O:11][C:12]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:13]=1[CH2:14][NH2:15]>C1(C)C=CC=CC=1>[CH3:10][O:11][C:12]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:13]=1[CH2:14][N:15]1[C:5](=[O:7])[CH2:4][CH:2]([C:1]([OH:9])=[O:8])[CH2:3]1

Participants

4

Reactant 2

HCID 811Itaconic acidHCID 5972502,4-Dimethoxybenzylamine

Product 1

HCID 112544611-(2,4-Dimethoxybenzyl)-5-oxopyrrolidine-3-carboxylic acidYield 71.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of itaconic acid (13.0 g, 100 mmol) in toluene (50 ml) was added a solution of 2,4-dimethoxybenzylamine (17.54 g, 105.0 mmol) in toluene (50 mL) and the reaction mixture was stirred for 15 h under reflux. The mixture was cooled to ambient temperature and then concentrated under reduced pressure. The residue was treated with diethyl ether (100 mL) and the resulting precipitate was collected by filtration, washed with diethyl ether and EtOAc and dried to afford 1-(2,4-dimethoxybenzyl)-5-oxopyrrolidine-3-carboxylic acid (20.0 g, 71% yield) as a colorless solid.

Workup

  1. temperatureunder reflux
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was treated with diethyl ether (100 mL)
  4. filtrationthe resulting precipitate was collected by filtration
  5. washwashed with diethyl ether and EtOAc
  6. customdried

Sources & evidence

ORD record
ord-3f437f78dbf04d2bace7d5716f7b7d9b
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Linked notes

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