Benzylamine → (3R,4R)-1-benzyl-3,4-dihydroxypyrrolidine-2,5-dione

HRID 1392752Notes

Reaction equation

HRID 1392752 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>[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 729946(3R,4R)-1-benzyl-3,4-dihydroxypyrrolidine-2,5-dione

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
150 °C

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 using a Dean-Stark trap. After the reaction mixture was allowed to cool overnight, crystals were collected by filtration and washed with acetone. The resultant crude product was recrystallized from ethanol to obtain the title compound (23.2 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto cool overnight
  3. filtrationcrystals were collected by filtration
  4. washwashed with acetone
  5. customThe resultant crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-49de5a595b77452a81a48f56ca6f4c68
Source dataset
uspto-grants-2008_03
Patent number
US07342014B2

Reaction notes

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