O-Xylene → 1-Benzyl-3,4-dihydroxypyrrolidine-2,5-dione

HRID 2104375Notes

Reaction equation

HRID 2104375 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.C1(C)C(C)=CC=CC=1>O>[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

5

Reactant 3

HCID 7237O-XyleneHCID 7504BenzylamineHCID 444305L-Tartaric acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

L-Tartaric acid (30 g) and benzylamine (22 mL) were added to xylene (150 mL), and the mixture was heated under reflux at 150° C. for 3 hours while water was removed with Dean-Stark apparatus. After the reaction mixture was left to cool overnight, the resultant crystals were collected by filtration, and were washed with acetone. The thus-obtained crude product was recrystallized from ethanol, to thereby give the title compound (23.2 g).

Workup

  1. temperaturethe mixture was heated
  2. customwas removed with Dean-Stark apparatus
  3. waitAfter the reaction mixture was left
  4. temperatureto cool overnight
  5. filtrationthe resultant crystals were collected by filtration
  6. washwere washed with acetone
  7. customThe thus-obtained crude product
  8. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-7de14233a581459fab736d7540c362d4
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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