Hydrochloric Acid → 1-Methyl-2-oxopyrrolidine-3-carboxylic acid

HRID 2241249Notes

Reaction equation

HRID 2241249 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([C:7]([O:9]C)=[O:8])[C:3]1=[O:11].C[Si](C)(C)[O-].[K+].Cl>C1COCC1>[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[C:3]1=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12646144Methyl 1-methyl-2-oxopyrrolidine-3-carboxylateHCID 23668039Potassium trimethylsilanolate

Product 1

HCID 148766891-Methyl-2-oxopyrrolidine-3-carboxylic acidYield 74.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 250 mL round-bottomed flask was charged with methyl 1-methyl-2-oxopyrrolidine-3-carboxylate (1.89 g, 12.0 mmol), potassium trimethylsilanolate (4.64 g, 36.1 mmol), and THF (100 mL). The reaction mixture was stirred at room temperature overnight, then HCl (50 mL, 2.0 M in Et2O) was added and the reaction mixture was stirred for 5 minutes. The solid was removed by filtration and the filtrate concentrated to give the crude product 1.28 g (74.2%), which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ 3.40-3.49 (m, 3H), 2.94 (s, 3H), 2.37-2.47 (m, 2H).

Workup

  1. stirringthe reaction mixture was stirred for 5 minutes
  2. customThe solid was removed by filtration
  3. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-df9d5679b5bf411e9078d818b55cd227
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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