HCID 57979780, compound → 1,1-Dimethylethyl 4-[3-(trifluoromethyl)-2-pyridinyl]-1-piperidinecarboxylate

HRID 716923Notes

Reaction equation

HRID 716923 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[C:4]([C:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH:10]=2)=[N:5][CH:6]=[CH:7][CH:8]=1>CO.[C].[Pd]>[F:22][C:2]([F:1])([F:23])[C:3]1[C:4]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:11][CH2:10]2)=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 57979780HCID 57979780, compound

Product 1

HCID 579797851,1-Dimethylethyl 4-[3-(trifluoromethyl)-2-pyridinyl]-1-piperidinecarboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 178418390HCID 178418390, compoundSolvent

Procedure

Into a 50-mL round-bottom flask was purged and maintained with an inert atmosphere of hydrogen, was added a solution of tert-butyl 4-(3-(trifluoromethyl)pyridin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (449.3 mg, 1.27 mmol, 1.00 equiv, 93%) in methanol (20 mL) and Palladium carbon anhydrous (134.8 mg). The resulting solution was stirred overnight at room temperature. The solids were filtered out. The resulting mixture was concentrated under vacuum. This resulted in 379.8 mg (87%) of tert-butyl 4-(3-(trifluoromethyl)pyridin-2-yl)piperidine-1-carboxylate as colorless oil.

Workup

  1. customInto a 50-mL round-bottom flask was purged
  2. temperaturemaintained with an inert atmosphere of hydrogen
  3. filtrationThe solids were filtered out
  4. concentrationThe resulting mixture was concentrated under vacuum
  5. customThis resulted in 379.8 mg (87%) of tert-butyl 4-(3-(trifluoromethyl)pyridin-2-yl)piperidine-1-carboxylate as colorless oil

Sources & evidence

ORD record
ord-e1abf4142f5a4d829586cf20a6421054
Source dataset
uspto-grants-2015_11
Patent number
US09193693B2

Reaction notes

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