tert-Butyl ((1-benzylpyrrolidin-3-yl)methyl)carbamate → tert-butyl N-((pyrrolidin-3-yl)methyl)carbamate

HRID 985238Notes

Reaction equation

HRID 985238 reaction equation
C([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:9]1)C1C=CC=CC=1>CCOC(C)=O.[OH-].[OH-].[Pd+2]>[NH:8]1[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:18])[CH3:20])[CH2:9]1

Participants

4

Reactant 1

HCID 5108694tert-Butyl ((1-benzylpyrrolidin-3-yl)methyl)carbamate

Product 1

HCID 4250767tert-butyl N-((pyrrolidin-3-yl)methyl)carbamateYield 90.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl (1-benzylpyrrolidin-3-yl)methylcarbamate (3.0 g, 10.33 mmole) in EtOAc (100 ml) was added Pd(OH)2 on carbon (0.3 g). The mixture was stirred under H2 balloon at room temperature for 3 h and filtered through Celite. The filtrate was concentrated to give colorless oil (1.87 g, 90%).

Workup

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-5b6508bd3a614bbc85f84c4c26824186
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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