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

HRID 595189Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][NH2:12].[CH3:13][O:14][C:15](=[O:23])[C:16](=[CH2:22])[CH2:17][C:18](OC)=[O:19]>CO>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][N:12]1[C:18](=[O:19])[CH2:17][CH:16]([C:15]([O:14][CH3:13])=[O:23])[CH2:22]1

Participants

Conditions

Temperature: 30 °C

Procedure

The mixture of 1-(2,4-dimethoxyphenyl)methanamine (5.2 g, 32 mmol) and 2-methylene-succinic acid dimethyl ester (5.0 g, 32 mmol) in MeOH (200 mL) was stirred at 30° C. for 10 hours. The solvent was removed under reduced pressure. The residue was recrystallized by petroleum ether to afford compound methyl 1-(2,4-dimethoxybenzyl)-5-oxopyrrolidine-3-carboxylate. 1H NMR (400 MHz, CDCl3) δ 7.13˜7.14 (m, 1H), 6.43-6.45 (m, 2H), 4.41-4.42 (m, 2H), 3.79-3.82 (m, 6H), 3.69 (s, 3H), 3.46-3.49 (m, 2H), 3.19-3.23 (m, 2H), 2.70-2.77 (m, 1H). MS ESI calc'd. for C15H20NO5 [M+H]+ 294. found 294.

Workup

customThe solvent was removed under reduced pressure
customThe residue was recrystallized by petroleum ether

Sources & evidence

ORD record: ord-41f2104fe368463099589f9c65ead434
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242984B2

Reaction notes

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