HCID 66731569, compound → HCID 66731652, compound

HRID 1963310Notes

Reaction equation

HRID 1963310 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:3]=1[CH2:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][N:14]=1)[C:8]([O:10][CH3:11])=[O:9]>C(O)(=O)C.[Pt](=O)=O>[F:1][C:2]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:3]=1[CH2:4][CH:5]1[CH2:6][CH:7]([C:8]([O:10][CH3:11])=[O:9])[CH2:12][CH2:13][NH:14]1

Participants

4

Reactant 1

HCID 66731569HCID 66731569, compound

Product 1

HCID 66731652HCID 66731652, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalyst2×HCID 176Acetic AcidSolvent

Procedure

A mixture of methyl 2-(2,5-difluorobenzyl)isonicotinate (6.8 g, 25.83 mmol) and platinum(IV) oxide (0.293 g, 1.29 mmol) in acetic acid (68 mL) was hydrogenated in a Büchi hydrogenator at room temperature and 5 bar for 5 h. More PtO2 (190 mg) was added and the hydrogenation continued at room temperature and 5 bar for additional 80 min. The reaction mixture was filtered through Celite and the catalyst was washed with methanol. The filtrate was concentrated, the residue was dissolved in DCM, washed with satd NaHCO3 and the organic layer was dried using a phase separator. The solvent was evaporated under reduced pressure. The residue was dissolved in iso-hexane/ether and filtered. The solvents were evaporated in vacuo to yield methyl 2-(2,5-difluorobenzyl)piperidine-4-carboxylate (6.65 g, 96%). MS m/z 270 (M+H)+

Workup

  1. customwas hydrogenated in a Büchi hydrogenator at room temperature
  2. customcontinued at room temperature
  3. wait5 bar for additional 80 min
  4. filtrationThe reaction mixture was filtered through Celite
  5. washthe catalyst was washed with methanol
  6. concentrationThe filtrate was concentrated
  7. dissolutionthe residue was dissolved in DCM
  8. washwashed with satd NaHCO3
  9. customthe organic layer was dried
  10. customThe solvent was evaporated under reduced pressure
  11. dissolutionThe residue was dissolved in iso-hexane/ether
  12. filtrationfiltered
  13. customThe solvents were evaporated in vacuo

Sources & evidence

ORD record
ord-2ee9df8d87c3420292c356ecde3cd87e
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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