Dimethyl itaconate → Methyl 1-(4-methoxybenzyl)-5-oxopyrrolidine-3-carboxylate

HRID 715925

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][CH:4]=1.[C:11]([O:20][CH3:21])(=[O:19])[C:12]([CH2:14][C:15](OC)=[O:16])=[CH2:13]>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]2[C:15](=[O:16])[CH2:14][CH:12]([C:11]([O:20][CH3:21])=[O:19])[CH2:13]2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of (4-methoxyphenyl)methanamine (6.9 g) and dimethyl itaconate (7.9 g) was stirred at 120° C. for 2 hours. After cooling, ethyl acetate was added to the reaction solution. The organic layer was washed with 1 N hydrochloric acid, a saturated aqueous solution of sodium bicarbonate, and saturated saline in this order and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (12.7 g).

Workup

temperatureAfter cooling
washThe organic layer was washed with 1 N hydrochloric acid
dry with materiala saturated aqueous solution of sodium bicarbonate, and saturated saline in this order and then dried over anhydrous sodium sulfate
distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-73eb7d946786429985ec642fa29e92f9
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187489B2

Linked notes

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