Dimethyl itaconate → Methyl 1-(2,4-dimethoxybenzyl)-5-oxopyrrolidine-3-carboxylate

HRID 645425Notes

Reaction equation

HRID 645425 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]([CH2:4][C:5]([O:7]C)=O)=[CH2:3].[CH3:12][O:13][C:14]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:15]=1[CH2:16][NH2:17]>CO>[CH3:11][O:10][C:1]([CH:2]1[CH2:4][C:5](=[O:7])[N:17]([CH2:16][C:15]2[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[CH:21][C:14]=2[O:13][CH3:12])[CH2:3]1)=[O:9]

Participants

4

Reactant 2

HCID 69240Dimethyl itaconateHCID 5972502,4-Dimethoxybenzylamine

Product 1

HCID 67439104Methyl 1-(2,4-dimethoxybenzyl)-5-oxopyrrolidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of dimethyl itaconate (4.08 g, 25.8 mmol) in MeOH (3.2 mL) was added to a solution of 2,4-dimethoxybenzylamine (4.32 g, 25.8 mmol) in MeOH (9.6 mL) via cannula at room temperature. After 18 h at room temperature the reaction was concentrated in vacuo to afford crude 1-(2,4-dimethoxybenzyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester as a viscous oil.

Workup

  1. concentrationAfter 18 h at room temperature the reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-c0e786ff61af410e86a07415ba9cb590
Source dataset
uspto-grants-2010_04
Patent number
US07705001B2

Reaction notes

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