Cumene → (S)-1-benzyl-3-hydroxypyrrolidine-2,5-dione

HRID 1081433Notes

Reaction equation

HRID 1081433 reaction equation
[C:1]([OH:9])(=O)[C@H:2]([CH2:4][C:5](O)=[O:6])[OH:3].[CH2:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1(C(C)C)C=CC=CC=1>O>[CH2:10]([N:17]1[C:5](=[O:6])[CH2:4][C@H:2]([OH:3])[C:1]1=[O:9])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7406CumeneHCID 7504BenzylamineHCID 222656L-Malic Acid

Product 1

HCID 10954694(S)-1-benzyl-3-hydroxypyrrolidine-2,5-dioneYield 39.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 50.0 g (0.373 mole) (S)-malic acid (Ia), 41 ml (0.373 mole) benzyl amine and 250 ml cumene was heated with an internal temperature of 155° C. for 2.5 h on a water separator, during which time 12 ml water were separated. An oily phase formed during cooling off which slowly crystallized. The cumene was decanted off thereafter and the residue crystallized out of 220 ml EtOH. 30.3 g (39.6%) (S)-1-benzyl-3-hydroxy-2,5-pyrrolidinedione (IIa) were isolated in the form of colorless crystals.

Workup

  1. customwere separated
  2. customAn oily phase formed
  3. temperatureduring cooling off which
  4. customslowly crystallized
  5. customThe cumene was decanted off
  6. customthe residue crystallized out of 220 ml EtOH

Sources & evidence

ORD record
ord-b610e96e4bf14fa2b45f8c820a93921d
Source dataset
uspto-grants-1996_12
Patent number
US05585500

Reaction notes

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