Methyl 2-(3,5-difluorobenzyl)isonicotinate → Methyl 2-(3,5-difluorobenzyl)piperidine-4-carboxylate

HRID 1963318Notes

Reaction equation

HRID 1963318 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([F:19])[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]=[C:17]([F:19])[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 66731588Methyl 2-(3,5-difluorobenzyl)isonicotinate

Product 1

HCID 66731630Methyl 2-(3,5-difluorobenzyl)piperidine-4-carboxylateYield 93.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

Methyl 2-(3,5-difluorobenzyl)isonicotinate (7.417 g, 28.18 mmol) was dissolved in acetic acid (72 mL) and platinum(IV) oxide (0.320 g, 1.41 mmol) was added. The mixture was hydrogenated in a Büchi hydrogenator at room temperature and 5 bar for 5 h. The reaction mixture was filtered through celite and the catalyst was washed with MeOH. The eluate was concentrated and DCM and 1 M K2CO3 were added. The phases were separated and the organic phase was washed with brine before it was dried and concentrated to yield methyl 2-(3,5-difluorobenzyl)piperidine-4-carboxylate (7.08 g, 93%). MS m/z 270 (M+H)+

Workup

  1. customwas hydrogenated in a Büchi hydrogenator at room temperature
  2. filtrationThe reaction mixture was filtered through celite
  3. washthe catalyst was washed with MeOH
  4. concentrationThe eluate was concentrated
  5. additionDCM and 1 M K2CO3 were added
  6. customThe phases were separated
  7. washthe organic phase was washed with brine before it
  8. customwas dried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-c1124d6c652f4db0ad7773f9028724bd
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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