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

HRID 83502Notes

Reaction equation

HRID 83502 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 90.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of itaconic acid (65.3 g) in toluene (400 ml) was added a solution of 2,4-dimethoxybenzylamine (84.0 g) in toluene (100 ml), and the mixture was stirred for 15 hours at reflux. This reaction solution was cooled to room temperature, and concentrated under reduced pressure. To the resulting residue was added diethyl ether (600 ml), and the mixture was stirred. The precipitated solid was collected by filtration, washed with diethyl ether and a small amount of ethyl acetate, and then dried under reduced pressure to give the titled compound (127 g).

Workup

  1. temperatureat reflux
  2. concentrationconcentrated under reduced pressure
  3. additionTo the resulting residue was added diethyl ether (600 ml)
  4. stirringthe mixture was stirred
  5. filtrationThe precipitated solid was collected by filtration
  6. washwashed with diethyl ether
  7. dry with materiala small amount of ethyl acetate, and then dried under reduced pressure

Sources & evidence

ORD record
ord-a20bf27265f24af68354a5a8fabe944b
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

Loading…