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

HRID 133605Notes

Reaction equation

HRID 133605 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>[C].[Pd].CO>[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-carboxylate

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

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

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. concentrationthe filtrate was then concentrated to thereby afford 4-[(glycylamino)methyl]-1-(tert- butoxycarbonyl)piperidine as a solid (3.84 g, 92%)

Sources & evidence

ORD record
ord-f738fac05dcc4b64bf09112fb2aac8c0
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Reaction notes

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