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

HRID 1910394Notes

Reaction equation

HRID 1910394 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]1[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH:12]=1>CO.[Pd]>[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1

Participants

4

Reactant 1

HCID 68598207tert-butyl 4-(1-methyl-1H-imidazol-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 23084145Tert-butyl 4-(1-methyl-1H-imidazol-2-yl)piperidine-1-carboxylateYield 32.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-(1-methyl-1H-imidazol-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate (398 mg) in MeOH (4.0 ml) was added 5% Pd/C (wet; 40 mg) and the mixture was stirred at room temperature for 7 hours under hydrogen atmosphere (1 atm). After removal of Pd/C with cerite, the filtrate was concentrated in vacuo. The resultant residue was purified by silica gel column (n-hexane:EtOAc=80:20 to EtOAc only) to give tert-butyl 4-(1-methyl-1H-imidazol-2-yl)piperidine-1-carboxylate (132 mg) as a colorless oil.

Workup

  1. customAfter removal of Pd/C with cerite, the filtrate
  2. concentrationwas concentrated in vacuo
  3. customThe resultant residue was purified by silica gel column (n-hexane

Sources & evidence

ORD record
ord-ac6b4f827b0c43d397d22a3a4a6f7bc0
Source dataset
uspto-grants-2013_12
Patent number
US08603975B2

Reaction notes

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