5-(4-Trifluoromethoxy-phenyl)-nicotinic acid methyl ester → Methyl 5-(4-(trifluoromethoxy)phenyl)piperidine-3-carboxylate

HRID 2091751Notes

Reaction equation

HRID 2091751 reaction equation
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[N:14][CH:15]=2)=[CH:6][CH:5]=1.[H][H]>C(O)C.[Pd]>[F:21][C:2]([F:1])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][NH:14][CH2:13][CH:12]([C:16]([O:18][CH3:19])=[O:17])[CH2:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 580025915-(4-Trifluoromethoxy-phenyl)-nicotinic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 58002737Methyl 5-(4-(trifluoromethoxy)phenyl)piperidine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

14 g (45 mmol) of methyl 5-[4-(trifluoromethoxy)phenyl]pyridine-3-carboxylate in ethanol (500 ml) were admixed with 17 g of moistened palladium/carbon catalyst (10% palladium, 50% water), and then hydrogenated at 60° C. and a 50 bar hydrogen atmosphere overnight. The reaction solution was filtered, the filter residue was washed with ethanol and the filtrate was concentrated under reduced pressure. The residue was purified by means of column chromatography (silica gel, dichloromethane/methanol 600:1→10:1). Yield: 8 g (59% of theory)

Workup

  1. customhydrogenated at 60° C.
  2. filtrationThe reaction solution was filtered
  3. washthe filter residue was washed with ethanol
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by means of column chromatography (silica gel, dichloromethane/methanol 600:1→10:1)

Sources & evidence

ORD record
ord-c7204bfc16f548058e7964ae8ce1448d
Source dataset
uspto-grants-2013_05
Patent number
US08440657B2

Reaction notes

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