Benzylamine → 1-Benzyl-3,4-dihydroxypyrrolidine-2,5-dione

HRID 456248Notes

Reaction equation

HRID 456248 reaction equation
[C:1]([OH:10])(=O)[C@@H:2]([C@H:4]([C:6](O)=[O:7])[OH:5])[OH:3].[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CC1C=CC=CC=1C>[CH2:11]([N:18]1[C:6](=[O:7])[C@H:4]([OH:5])[C@@H:2]([OH:3])[C:1]1=[O:10])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 444305L-Tartaric acid

Product 1

HCID 7299461-Benzyl-3,4-dihydroxypyrrolidine-2,5-dione

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

L-Tartaric acid (90 g, 600 mmol) and benzylamine (64.3 g, 600 mmol) were mixed in 400 mL of o-xylene and the mixture was refluxed 14 hours with a Dean-Stark trap. The pellet was filtered off and the compound was crystallized from hot EtOH (1600 mL). The formed crystals were washed with cold hexane to afford the title compound.

Workup

  1. temperaturethe mixture was refluxed 14 hours with a Dean-Stark trap
  2. filtrationThe pellet was filtered off
  3. customthe compound was crystallized from hot EtOH (1600 mL)
  4. washThe formed crystals were washed with cold hexane

Sources & evidence

ORD record
ord-4a13d574e19143a398a636b59ee0b19a
Source dataset
uspto-grants-2013_07
Patent number
US08497383B2

Reaction notes

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