(3S)-2-{[(1,1-dimethylethyl)oxy]carbonyl}-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid → (S)-2-(tert-Butoxycarbonyl)pyrazolidine-3-carboxylic acid

HRID 1396868Notes

Reaction equation

HRID 1396868 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[C@H:12]([C:13]([OH:15])=[O:14])[CH2:11][CH2:10][N:9]1C(OCC1C=CC=CC=1)=O)=[O:7])([CH3:4])[CH3:3]>CO.[OH-].[OH-].[Pd+2]>[CH3:4][C:2]([O:5][C:6]([N:8]1[C@H:12]([C:13]([OH:15])=[O:14])[CH2:11][CH2:10][NH:9]1)=[O:7])([CH3:1])[CH3:3]

Participants

4

Reactant 1

HCID 68287732(3S)-2-{[(1,1-dimethylethyl)oxy]carbonyl}-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid

Product 1

HCID 58501748(S)-2-(tert-Butoxycarbonyl)pyrazolidine-3-carboxylic acidYield 91%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a 100 ml round bottom flask was added (3S)-2-{[(1,1-dimethylethyl)oxy]carbonyl}-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid (1.84 g, 5.25 mmol) in methanol (30 mL), followed by Pd(OH)2 on carbon (20%, wet) (24.7 mg, 0.035 mmol). The mixture was degassed and stirred under an H2 atmosphere (balloon) at room temperature until LCMS indicated completion of the reaction (1 h). The catalyst was filtered off, and the filtrate was concentrated under vacuum to afford (3S)-2-{[(1,1-dimethylethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid (1.03 g, 4.77 mmol, 91% yield) as an off white solid.

Workup

  1. customThe mixture was degassed
  2. customcompletion of the reaction (1 h)
  3. filtrationThe catalyst was filtered off
  4. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-a8db6e5acd7c49c98d1e8f1ea838906e
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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