Water → 1-Methyl-3-pyrazolidinecarboxylic acid

HRID 1396885Notes

Reaction equation

HRID 1396885 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([C:7]([O:9]C(C)(C)C)=[O:8])[N:3]1C(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O.O>ClCCl>[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[NH:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 68287657Bis(1,1-dimethylethyl) 2-methyl-1,5-pyrazolidinedicarboxylate

Product 1

HCID 682879511-Methyl-3-pyrazolidinecarboxylic acidYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of bis(1,1-dimethylethyl) 2-methyl-1,5-pyrazolidinedicarboxylate dissolved in dichloromethane (DCM) (25 mL) was added TFA (30.7 mL, 398 mmol) and water (3.59 mL, 199 mmol). The reaction was stirred at rt and monitored by LCMS. When the reaction was deemed complete, the solvent was evaporated under reduced pressure to give a residue which was azeotroped from toluene (50 mL×3) in order to remove the TFA and water. The crude product was obtained as a colorless oil (97% yield based on TFA Salt), which was used directly for the next step. LC-MS (ES) m/e 130.9 (M+H)+.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customto give a residue which
  3. customwas azeotroped from toluene (50 mL×3) in order
  4. customto remove the TFA and water

Sources & evidence

ORD record
ord-6532b9850b1f4feebbb5ba97da370820
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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