Methyl 2-oxopyrrolidine-3-carboxylate → 2-Oxopyrrolidine-3-carboxylic acid

HRID 1676346Notes

Reaction equation

HRID 1676346 reaction equation
[O:1]=[C:2]1[CH:6]([C:7]([O:9]C)=[O:8])[CH2:5][CH2:4][NH:3]1.C[Si](C)(C)[O-].[K+]>C1COCC1>[O:1]=[C:2]1[CH:6]([C:7]([OH:9])=[O:8])[CH2:5][CH2:4][NH:3]1

Participants

4

Reactant 2

HCID 4738123Methyl 2-oxopyrrolidine-3-carboxylateHCID 23668039Potassium trimethylsilanolate

Product 1

HCID 134743702-Oxopyrrolidine-3-carboxylic acidYield 41.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A flask was charged with methyl 2-oxopyrrolidine-3-carboxylate (500 mg, 3.49 mmol), potassium trimethylsilanolate (1344 mg, 10.48 mmol) and THF (10 mL). The reaction mixture was stirred at room temperature until the starting material had been consumed (overnight). Then HCl (20 mL, 2.0M in Et2O) was added and the mixture was stirred for 30 minutes. Then the mixture was filtered to remove the solid and the solvent was removed under reduced pressure to give the crude product (188.7 mg, 41.84%), which was used for next step without further purification.

Workup

  1. customhad been consumed (overnight)
  2. additionThen HCl (20 mL, 2.0M in Et2O) was added
  3. stirringthe mixture was stirred for 30 minutes
  4. filtrationThen the mixture was filtered
  5. customto remove the solid
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-804c4a792f2445f8af8aca901c5afa6f
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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