Methyl 2-(3-fluoro-4-(trifluoromethyl)benzyl)isonicotinate → HCID 66731785, compound

HRID 1963332Notes

Reaction equation

HRID 1963332 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[C:19]([F:22])([F:21])[F:20])[CH2:5][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][N:15]=1)[C:9]([O:11][CH3:12])=[O:10]>C(O)(=O)C.[Pt](=O)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[C:19]([F:22])([F:20])[F:21])[CH2:5][CH:6]1[CH2:7][CH:8]([C:9]([O:11][CH3:12])=[O:10])[CH2:13][CH2:14][NH:15]1

Participants

4

Reactant 1

HCID 66731596Methyl 2-(3-fluoro-4-(trifluoromethyl)benzyl)isonicotinate

Product 1

HCID 66731785HCID 66731785, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of methyl 2-(3-fluoro-4-(trifluoromethyl)benzyl)isonicotinate (8.26 g, 26.37 mmol) in acetic acid (50 mL) was added platinum(IV) oxide (0.44 g, 1.94 mmol) and the resulting mixture hydrogenated at 5 bar in a Büchi hydrogenator for 8 h. The reaction mixture was filtered through a diatomeous earth filter carton and the catalyst washed with methanol. The solvents were evaporated, the residue dissolved in DCM and washed with 10% Na2CO3. After phase separation the aqueous layer was extracted with DCM. The combined organic layers were dried over MgSO4 and evaporated. Methyl 2-(3-fluoro-4-(trifluoromethyl)-benzyl)piperidine-4-carboxylate (8.4 g, 100%) was isolated as a pale yellow oil that partially solidified upon standing. MS m/z 320 (M+H)+

Workup

  1. filtrationThe reaction mixture was filtered through a diatomeous earth
  2. filtrationfilter carton
  3. washthe catalyst washed with methanol
  4. customThe solvents were evaporated
  5. dissolutionthe residue dissolved in DCM
  6. washwashed with 10% Na2CO3
  7. customAfter phase separation the aqueous layer
  8. extractionwas extracted with DCM
  9. dry with materialThe combined organic layers were dried over MgSO4
  10. customevaporated

Sources & evidence

ORD record
ord-1aa175a209f44c819e114ed7274a6536
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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