Methyl 2-(3-fluorobenzyl)isonicotinate → Methyl 2-(3-fluorobenzyl)piperidine-4-carboxylate

HRID 1963271Notes

Reaction equation

HRID 1963271 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[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][CH:18]=1)[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 66731557Methyl 2-(3-fluorobenzyl)isonicotinate

Product 1

HCID 66732105Methyl 2-(3-fluorobenzyl)piperidine-4-carboxylateYield 110%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalyst2×HCID 176Acetic AcidSolvent

Procedure

Methyl 2-(3-fluorobenzyl)isonicotinate (6.766 g, 27.59 mmol) was dissolved in acetic acid (70 mL) and platinum(IV) oxide (0.313 g, 1.38 mmol) added. The resulting mixture was hydrogenated in a Büchi hydrogenator at room temperature and 5 bar for 4.5 h. More platinum(IV) oxide (0.313 g, 1.38 mmol) was added and the hydrogenation continued at 5 bar for 2 h 40 min. The catalyst was filtered off, washed with MeOH and the eluate evaporated. DCM and 10% K2CO3 were added and the phases separated. The water phase was extracted with DCM and the combined organic phase washed with brine, passed through a phase separator and evaporated to yield crude methyl 2-(3-fluorobenzyl)piperidine-4-carboxylate (7.6 g, 110%) as a brown oil. MS m/z 252 (M+H)+

Workup

  1. customwas hydrogenated in a Büchi hydrogenator at room temperature
  2. waitthe hydrogenation continued at 5 bar for 2 h 40 min
  3. filtrationThe catalyst was filtered off
  4. washwashed with MeOH
  5. additionDCM and 10% K2CO3 were added
  6. customthe phases separated
  7. extractionThe water phase was extracted with DCM
  8. washthe combined organic phase washed with brine
  9. customevaporated

Sources & evidence

ORD record
ord-503838eba98c408ca43062ac217e6b5f
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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