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

HRID 1500916Notes

Reaction equation

HRID 1500916 reaction equation
[CH2:1]=[C:2]([CH2:7][C:8]([O:10]C)=O)[C:3]([O:5][CH3:6])=[O:4].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][NH2:21])=[CH:16][CH:15]=1>CO>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]2[C:8](=[O:10])[CH2:7][CH:2]([C:3]([O:5][CH3:6])=[O:4])[CH2:1]2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 69240Dimethyl itaconateHCID 754524-Methoxybenzylamine

Product 1

HCID 4093874Methyl 1-(4-methoxybenzyl)-5-oxopyrrolidine-3-carboxylateYield 86.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of dimethyl 2-methylidenebutanedioate (47.5 g, 300 mmol) and 1-(4-methoxyphenyl)methanamine (41.2 g, 300 mmol) in 400 mL of MeOH was stirred at room temperature overnight. The resulting reaction mixture was concentrated in vacuo to remove methanol. The residual brown oil was stirred with 40 mL of EtOAc and 40 mL of PE vigorously. The precipitate was collected by filtration and washed with PE (40 mL×2) to afford methyl 1-(4-methoxybenzyl)-5-oxopyrrolidine-3-carboxylate (68.0 g, yield: 86.1%).

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated in vacuo
  3. customto remove methanol
  4. stirringThe residual brown oil was stirred with 40 mL of EtOAc and 40 mL of PE vigorously
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with PE (40 mL×2)

Sources & evidence

ORD record
ord-a6c4d8531c9844b596de401aaeb8be4d
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

Loading…