Methyl chloroformate → 1-Pyrrolidinecarboxylic acid, 2,5-dioxo-, methyl ester

HRID 1493825Notes

Reaction equation

HRID 1493825 reaction equation
[C:1]1(=[O:7])[NH:5][C:4](=[O:6])[CH2:3][CH2:2]1.CN1CCOCC1.[CH3:15][O:16][C:17](Cl)=[O:18]>C1COCC1>[CH3:15][O:16][C:17]([N:5]1[C:4](=[O:6])[CH2:3][CH2:2][C:1]1=[O:7])=[O:18]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 79724-MethylmorpholineHCID 11439Succinimide

Product 1

HCID 123002841-Pyrrolidinecarboxylic acid, 2,5-dioxo-, methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 19.8 g (200 mmole) of succinimide and 22 ml (200 mmole) of N-methylmorpholine in 350 ml THF at -5° was added 15.5 ml (200 mmole) methylchloroformate over 20 minutes. After stirring for two hours at 25°, the solvent was removed under reduced pressure and the residue was taken up in EtOAc. The suspension was filtered, and washed with saturated NaCl, saturated NaHCO3, and saturated NaCl. After drying, the solution was concentrated under reduced pressure and Et2O was added, giving the product as a crystalline solid, 10.0 g. The structure was confirmed by NMR and mass spectroscopy.

Workup

  1. customthe solvent was removed under reduced pressure
  2. filtrationThe suspension was filtered
  3. washwashed with saturated NaCl, saturated NaHCO3, and saturated NaCl
  4. customAfter drying
  5. concentrationthe solution was concentrated under reduced pressure and Et2O
  6. additionwas added

Sources & evidence

ORD record
ord-1fe1462e570844fb999a7f50d54afe94
Source dataset
uspto-grants-1991_06
Patent number
US05024994

Reaction notes

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