tert-butyl 4-(2-methoxyphenyl)-5,6-dihydropyridine-1(2H)-carboxylate → Tert-butyl 4-(2-methoxyphenyl)piperidine-1-carboxylate

HRID 2223703Notes

Reaction equation

HRID 2223703 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 22629561tert-butyl 4-(2-methoxyphenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 22629567Tert-butyl 4-(2-methoxyphenyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(2-methoxy-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (200 mg, 0.69 mmol), Pd—C 10% (30 mg) in EtOAc (5 mL) is hydrogenated at room temperature and atmospheric pressure for 20 h. The mixture is filtered over Celite, and the filtrate is evaporated to provide the title compound.

Workup

  1. customis hydrogenated at room temperature
  2. filtrationThe mixture is filtered over Celite
  3. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-bffb5ce94b3d46f38d9b76633b0316df
Source dataset
uspto-grants-2008_05
Patent number
US07375227B2

Reaction notes

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