2,4-Dimethoxybenzylamine → 4-methyl-5-oxopyrrolidine-3-carboxylic Acid

HRID 83482Notes

Reaction equation

HRID 83482 reaction equation
C[O:2][C:3](=O)[CH:4]([CH3:11])[C:5](=[CH2:10])[C:6]([O:8]C)=[O:7].COC1C=C(OC)C=CC=1C[NH2:18]>C1(C)C=CC=CC=1>[CH3:11][CH:4]1[C:3](=[O:2])[NH:18][CH2:10][CH:5]1[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 5972502,4-DimethoxybenzylamineHCID 126883221,4-Dimethyl 2-methyl-3-methylidenebutanedioate

Product 1

HCID 836706874-methyl-5-oxopyrrolidine-3-carboxylic AcidYield 174.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-methyl-3-methylenesuccinic acid dimethyl ester (9.81 g) in toluene (100 ml) was added 2,4-dimethoxybenzylamine (9.72 g) and the mixture was stirred for 3 days at reflux. This reaction solution was cooled to room temperature and then purified by silica gel column chromatography (eluent: n-hexane/chloroform=1/1 to 0/1) to give the titled compound (14.2 g).

Workup

  1. temperatureat reflux
  2. custompurified by silica gel column chromatography (eluent: n-hexane/chloroform=1/1 to 0/1)

Sources & evidence

ORD record
ord-0e518fcb4b674dbba497bf5d95a8e241
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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