Itaconic acid → 1-Benzyl-5-oxo-pyrrolidine-3-carboxylic acid

HRID 1253514Notes

Reaction equation

HRID 1253514 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]([CH2:4][C:5](O)=[O:6])=[CH2:3].[CH2:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O>[CH2:10]([N:17]1[C:5](=[O:6])[CH2:4][CH:2]([C:1]([OH:9])=[O:8])[CH2:3]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 811Itaconic acidHCID 7504Benzylamine

Product 1

HCID 990241-Benzyl-5-oxo-pyrrolidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of itaconic acid (130 g, 1.00 mol) and benzylamine (107 g, 1.00 mol) were heated to 130° C. After 30 minutes, the reaction mixture was cooled and diluted with water (200 mL). The resulting slurry was filtered, washed with cold water, dissolved in aqueous sodium hydroxide, and treated with active carbon. The slurry was filtered to remove the carbon, and the aqueous solution was acidified with hydrochloric acid to precipitate solids. The solids were recrystallized from ethanol to afford 1-benzyl-5-oxopyrrolidine-3-carboxylic acid that was used without additional purification.

Workup

  1. temperaturethe reaction mixture was cooled
  2. filtrationThe resulting slurry was filtered
  3. washwashed with cold water
  4. dissolutiondissolved in aqueous sodium hydroxide
  5. additiontreated with active carbon
  6. filtrationThe slurry was filtered
  7. customto remove the carbon
  8. customto precipitate solids
  9. customThe solids were recrystallized from ethanol

Sources & evidence

ORD record
ord-7fb28e03836c4f37a8fa570fc1325d29
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

Loading…