Methanol → [4-(4-Amino-3-methoxy-phenyl)-piperidin-1-yl]-acetic acid tert-butyl ester

HRID 1262347Notes

Reaction equation

HRID 1262347 reaction equation
[C:1]([O:5][C:6](=[O:25])[CH2:7][N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[C:16]([O:23][CH3:24])[CH:15]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].CO>[Pd]>[C:1]([O:5][C:6](=[O:25])[CH2:7][N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([O:23][CH3:24])[CH:15]=2)[CH2:12][CH2:13]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 66712420[4-(3-Methoxy-4-nitro-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-acetic acid tert-butyl ester

Product 1

HCID 66711699[4-(4-Amino-3-methoxy-phenyl)-piperidin-1-yl]-acetic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of [4-(3-Methoxy-4-nitro-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-acetic acid tert-butyl ester (145 mg, 0.416 mmol) in methanol (15 mL, 370 mmol) was added 10% Palladium on Carbon (50% Wet, 44.3 mg, 0.0208 mmol). The mixture was shaken in a Parr apparatus under an atmosphere of Hydrogen (50 PSI) for 3 h. Filtration through Celite and evaporation of the solvent provided crude [4-(4-Amino-3-methoxy-phenyl)-piperidin-1-yl]-acetic acid tert-butyl ester, which was used without further purification.

Workup

  1. filtrationFiltration
  2. customthrough Celite and evaporation of the solvent

Sources & evidence

ORD record
ord-deb49dabc9ac45baa801fa9425c58f33
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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