Benzylamine → (3R,4R)-1-benzyl-3,4-dihydroxypyrrolidine-2,5-dione
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- temperaturethe mixture was refluxed 14 hours with a Dean-Stark trap
- filtrationThe pellet was filtered off
- customthe compound was crystallized from hot EtOH (1600 mL)
- 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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