tert-butyl 4-(4-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate → Tert-butyl 4-[4-(trifluoromethyl)phenyl]piperidine-1-carboxylate

HRID 522855Notes

Reaction equation

HRID 522855 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]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[CH:16][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 18364827tert-butyl 4-(4-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 11301928Tert-butyl 4-[4-(trifluoromethyl)phenyl]piperidine-1-carboxylateYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 4-(4-trifluoromethyl-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (2.5 g, 0.00783 mol) (prepared as described in Reference G above) in ethanol (23.0 mL) was added 10% Pd/C (826 mg, 0.00078 mol) under N2 atmosphere and the mixture was allowed to stir at RT overnight under hydrogen atmosphere. The reaction mixture was filtered through cellite, washing with EtOAc (2×100 mL). The filtrate was concentrated under reduced pressure to obtain 4-(4-trifluoromethyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (2 g, 80%).

Workup

  1. filtrationThe reaction mixture was filtered through cellite
  2. washwashing with EtOAc (2×100 mL)
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-033d881bab674d9cb293bd215b1fc8ec
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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