tert-butyl 4-(1H-imidazol-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate → tert-butyl 4-(1H-imidazol-2-yl)piperidine-1-carboxylate

HRID 1725769Notes

Reaction equation

HRID 1725769 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH:11]=1>[Pd].C(O)C>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1

Participants

4

Reactant 1

HCID 69053296tert-butyl 4-(1H-imidazol-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 17840015tert-butyl 4-(1H-imidazol-2-yl)piperidine-1-carboxylateYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of tert-butyl 4-(1H-imidazol-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate (7.5 g) and palladium on carbon (10%, 1 g) in ethanol (150 mL) was hydrogenated at 30 psi overnight. The catalyst was removed by filtration through celite and the filtrate was evaporated to give tert-butyl 4-(1H-imidazol-2-yl)piperidine-1-carboxylate (7.5 g).

Workup

  1. customwas hydrogenated at 30 psi overnight
  2. customThe catalyst was removed by filtration through celite
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-b5455f3b58794e18851cd3d8ae8c03ae
Source dataset
uspto-grants-2009_02
Patent number
US07491737B2

Reaction notes

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