HCID 66731874, compound → HCID 66731633, compound

HRID 1963267Notes

Reaction equation

HRID 1963267 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][N:16]=2)[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1>C(O)(=O)C.[Pt](=O)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[CH2:8][CH:9]([C:10]([O:12][CH3:13])=[O:11])[CH2:14][CH2:15][NH:16]2)=[CH:17][CH:18]=1

Participants

4

Reactant 1

HCID 66731874HCID 66731874, compound

Product 1

HCID 66731633HCID 66731633, compoundYield 73.6%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

Methyl 2-(4-fluorobenzyl)isonicotinate (5.06 g, 20.63 mmol) was dissolved in acetic acid (50 mL) and platinum(IV) oxide (0.234 g, 1.03 mmol) added. The resulting mixture was hydrogenated in a Büchi hydrogenator overnight at room temperature and 5 bar. The catalyst was filtered off and washed with MeOH and the eluate evaporated. DCM and 10% K2CO3 were added and the phases separated. The aqueous phase was extracted with DCM and the combined organic phase washed with brine, passed through a phase separator and evaporated to yield methyl 2-(4-fluorobenzyl)piperidine-4-carboxylate (3.816 g, 73.6%) as a yellow oil. MS m/z 252 (M+H)+

Workup

  1. customwas hydrogenated in a Büchi hydrogenator overnight 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. extractionThe aqueous phase was extracted with DCM
  7. washthe combined organic phase washed with brine
  8. customevaporated

Sources & evidence

ORD record
ord-1e21b8b5256c482290575b1715034d1f
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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