4-[4-(1-Methoxycarbonyl-ethyl)-phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester → 4-[4-(1-Methoxycarbonyl-ethyl)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 409724Notes

Reaction equation

HRID 409724 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]([C:22]([O:24][CH3:25])=[O:23])[CH3:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:15]=[CH:16][C:17]([CH:20]([C:22]([O:24][CH3:25])=[O:23])[CH3:21])=[CH:18][CH:19]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 866861114-[4-(1-Methoxycarbonyl-ethyl)-phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 866861124-[4-(1-Methoxycarbonyl-ethyl)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

18.0 g (52.1 mmol) 4-[4-(1-Methoxycarbonyl-ethyl)-phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (VII.1) in 400 mL methanol are hydrogenated for 1 h at rt using 5.55 g (5.21 mmol) Pd/C. After that time, the catalyst is filtered off (celite) and the solvent is evaporated. The residue is purified by column chromatography (silica gel; heptane:EtOAc gradient 100:0->60:40).

Workup

  1. filtrationAfter that time, the catalyst is filtered off (celite)
  2. customthe solvent is evaporated
  3. customThe residue is purified by column chromatography (silica gel; heptane:EtOAc gradient 100:0->60:40)

Sources & evidence

ORD record
ord-9b9b9294ebc249798b83382d2a76e382
Source dataset
uspto-grants-2014_06
Patent number
US08759528B2

Reaction notes

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