4-[{(N-(benzyloxycarbonyl)glycyl)amino}methyl]1-(tert-butoxycarbonyl)piperidine → tert-Butyl 4-((2-aminoacetamido)methyl)piperidine-1-carboxylate

HRID 279318Notes

Reaction equation

HRID 279318 reaction equation
C(OC([NH:11][CH2:12][C:13]([NH:15][CH2:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]1)=[O:14])=O)C1C=CC=CC=1>CO.[Pd]>[NH2:11][CH2:12][C:13]([NH:15][CH2:16][CH:17]1[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH2:22]1)=[O:14]

Participants

4

Reactant 1

HCID 117111694-[{(N-(benzyloxycarbonyl)glycyl)amino}methyl]1-(tert-butoxycarbonyl)piperidine

Product 1

HCID 11701760tert-Butyl 4-((2-aminoacetamido)methyl)piperidine-1-carboxylateYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-[{(N-(benzyloxycarbonyl)glycyl)amino}methyl]-1-(tert-butoxycarbonyl)piperidine (6.26 g, 15.4 mmol) in methanol (100 mL) was hydrogenated at 1 atm in the presence of 5% palladium on charcoal (620 mg) at room temperature for 7 h. The catalyst was removed by filtration through Celite and the combined filtrate was concentrated to afford 4-{(glycylamino)methyl}-1-(tert-butoxycarbonyl)piperidine (3.84 g, 92%) as a solid.

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. concentrationthe combined filtrate was concentrated

Sources & evidence

ORD record
ord-ed3ab0285f92443db35ddbfd3a8d494f
Source dataset
uspto-grants-2002_03
Patent number
US06362177B1

Reaction notes

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