Benzyl 3-(tert-butoxycarbonylamino)piperidine-1-carboxylate → 3-(Boc-amino)piperidine

HRID 2115744Notes

Reaction equation

HRID 2115744 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][N:11](C(OCC2C=CC=CC=2)=O)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[NH:11]1[CH2:12][CH2:13][CH2:14][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:10]1

Participants

4

Reactant 1

HCID 22258937Benzyl 3-(tert-butoxycarbonylamino)piperidine-1-carboxylate

Product 1

HCID 42330413-(Boc-amino)piperidineYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of benzyl 3-[(tert-butoxycarbonyl)amino]-1-piperidinecarboxylate (2.25 g, 6.73 mmol) and 10% Pd/C (0.229 g) in EtOH (20 mL) was stirred at room temperature under a hydrogen atmosphere (1 atm) for 14 hrs. The catalyst was removed by filtration through Celite®, and the filtrate was concentrated under reduced pressure to give tert-butyl 3-piperidinylcarbamate as a solid (1.22 g, yield; 91%).

Workup

  1. customThe catalyst was removed by filtration through Celite®
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-45d2bc0ac56e4e3a8f4d29b47be2c131
Source dataset
uspto-grants-2008_10
Patent number
US07435743B2

Reaction notes

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