(2S)-1,1,1-trifluoropropan-2-yl [(3S)-1-benzylpyrrolidin-3-yl]carbamate → (2S)-1,1,1-trifluoropropan-2-yl (3S)-pyrrolidin-3-ylcarbamate

HRID 452858Notes

Reaction equation

HRID 452858 reaction equation
C([N:8]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14](=[O:22])[O:15][C@@H:16]([CH3:21])[C:17]([F:20])([F:19])[F:18])[CH2:9]1)C1C=CC=CC=1>C1COCC1.CO.[OH-].[OH-].[Pd+2]>[NH:8]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14](=[O:22])[O:15][C@@H:16]([CH3:21])[C:17]([F:20])([F:18])[F:19])[CH2:9]1

Participants

5

Reactant 1

HCID 68029098(2S)-1,1,1-trifluoropropan-2-yl [(3S)-1-benzylpyrrolidin-3-yl]carbamate

Product 1

HCID 66697914(2S)-1,1,1-trifluoropropan-2-yl (3S)-pyrrolidin-3-ylcarbamate

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S)-1,1,1-trifluoropropan-2-yl [(3S)-1-benzylpyrrolidin-3-yl]carbamate (1.82 g) in THF (20 ml) and MeOH (20 ml) was added 20% palladium hydroxide on activated carbon (200 mg). The resulting solution was placed under a H2 atmosphere (balloon pressure) and stirred at room temperature for 15 hours. The solution was obtained by filtration through Celite and, washing the filter cake with MeOH, was concentrated in vacuo to give (2S)-1,1,1-trifluoropropan-2-yl(3S)-pyrrolidin-3-ylcarbamate as a pale yellow oil.

Workup

  1. customThe solution was obtained by filtration through Celite
  2. washwashing the filter cake with MeOH
  3. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-6780355a699848f7a6255a2ab25e3e63
Source dataset
uspto-grants-2013_07
Patent number
US08492397B2

Reaction notes

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