Benzylamine → HCID 729944, compound

HRID 618179Notes

Reaction equation

HRID 618179 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=CC=C(C)C=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 7504BenzylamineHCID 7929M-XyleneHCID 439655D-Tartaric acid

Product 1

HCID 729944HCID 729944, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of D(-)-tartaric acid (4.5 g, 30 mmol), benzylamine (3.3 ml, 30,2 mmol) and m-xylene (50 ml) was heated at reflux temperature for 4 hours with simultaneous capture of water. The mixture was cooled to room temperature, filtered and washed with m-xylene twice (2×2 ml) and acetone (10 ml) to give (3S,4S)-1-benzyl-3,4-dihydroxy-2,5-dioxopyrrolidine (5.0 g, yield: 76%) as light yellow crystals.

Workup

  1. temperaturewas heated
  2. filtrationfiltered
  3. washwashed with m-xylene twice (2×2 ml) and acetone (10 ml)

Sources & evidence

ORD record
ord-e37e78a46ce24161a2001acd5afc726d
Source dataset
uspto-grants-1999_09
Patent number
US05952363

Reaction notes

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