tert-butyl 5-(1-methyl-1H-pyrazol-5-yl)-3,4-dihydropyridine-1(2H)-carboxylate → tert-butyl 3-(1-methyl-1H-pyrazol-5-yl)piperidine-1-carboxylate

HRID 1530603Notes

Reaction equation

HRID 1530603 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH2:8][CH2:9][CH2:10][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:12]=2)=[CH:5][CH:4]=[N:3]1>CO.[Pd]>[CH3:1][N:2]1[C:6]([CH:7]2[CH2:8][CH2:9][CH2:10][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:12]2)=[CH:5][CH:4]=[N:3]1

Participants

4

Reactant 1

HCID 68312723tert-butyl 5-(1-methyl-1H-pyrazol-5-yl)-3,4-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 68313066tert-butyl 3-(1-methyl-1H-pyrazol-5-yl)piperidine-1-carboxylateYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 5-(1-methyl-1H-pyrazol-5-yl)-3,4-dihydropyridine-1(2H)-carboxylate (800 mg, 3.00 mmol) in MeOH (20 mL) was added 10% Pd/C (80 mg). The reaction mixture was stirred under H2 (1 atm) for 16 h. After concentration, the residue was purified by silica gel chromatography eluting with a 0-30% gradient of EtOAc in petroleum ether to give tert-butyl 3-(1-methyl-1H-pyrazol-5-yl)piperidine-1-carboxylate (0.68 g, 86% yield) as pale yellow oil. LCMS (ESI) m/z: 265.2 [M+H+]

Workup

  1. concentrationAfter concentration
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with a 0-30% gradient of EtOAc in petroleum ether

Sources & evidence

ORD record
ord-d0614013714d441c80d4fd4c8fbd8447
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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