Methyl 2-(2,4,5-trifluorophenyl)isonicotinate → Methyl 2-(2,4,5-trifluorophenyl)piperidine-4-carboxylate

HRID 1963201Notes

Reaction equation

HRID 1963201 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][N:19]=1)[C:13]([O:15][CH3:16])=[O:14]>C(O)(=O)C.[Pt](=O)=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[CH:10]1[CH2:11][CH:12]([C:13]([O:15][CH3:16])=[O:14])[CH2:17][CH2:18][NH:19]1

Participants

4

Reactant 1

HCID 66732429Methyl 2-(2,4,5-trifluorophenyl)isonicotinate

Product 1

HCID 66731764Methyl 2-(2,4,5-trifluorophenyl)piperidine-4-carboxylateYield 95%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

Methyl 2-(2,4,5-trifluorophenyl)isonicotinate (2.509 g, 9.39 mmol) was dissolved in acetic acid (25 mL) and platinum(IV) oxide (0.107 g, 0.47 mmol) added. The resulting mixture was hydrogenated in a Büchi hydrogenator at room temperature and 5 bar for 6 h. The catalyst was filtered off, washed with MeOH and the eluate evaporated. DCM and 10% K2CO3 were added and the phases separated. The organic layer was washed with brine, passed through a phase separator and evaporated to yield methyl 2-(2,4,5-trifluorophenyl)piperidine-4-carboxylate (2.434 g, 95%) as a brown oil. MS m/z 274 (M+H)+

Workup

  1. customwas hydrogenated in a Büchi hydrogenator at room temperature
  2. filtrationThe catalyst was filtered off
  3. washwashed with MeOH
  4. additionDCM and 10% K2CO3 were added
  5. customthe phases separated
  6. washThe organic layer was washed with brine
  7. customevaporated

Sources & evidence

ORD record
ord-fd3e8c6d28784dd3b04a301edc1053f4
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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