HCID 66732259, compound → HCID 66731779, compound

HRID 1963142Notes

Reaction equation

HRID 1963142 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][N:18]=2)[C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:7][CH:8]=1>C(O)(=O)C.[Pt](=O)=O>[F:19][C:2]([F:1])([F:20])[C:3]1[CH:4]=[C:5]([CH:9]2[CH2:10][CH:11]([C:12]([O:14][CH3:15])=[O:13])[CH2:16][CH2:17][NH:18]2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 66732259HCID 66732259, compound

Product 1

HCID 66731779HCID 66731779, compoundYield 52.7%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

Methyl 2-(3-(trifluoromethyl)phenyl)isonicotinate (2.6 g, 9.25 mmol) was dissolved in acetic acid (40 mL) and platinum(IV) oxide (0.210 g, 0.92 mmol) added. The resulting mixture was hydrogenated in a Büchi hydrogenator at room temperature and 5 bar for 3 h. The catalyst was filtered off, washed with MeOH and the eluate evaporated. DCM and 1 M K2CO3 were added and the phases separated. The organic layer was washed with brine, passed through a phase separator and evaporated to yield methyl 2-(3-(trifluoromethyl)phenyl)piperidine-4-carboxylate (1.4 g, 52%) as a slightly brown oil. MS m/z 288 (M+H)+

Workup

  1. customwas hydrogenated in a Büchi hydrogenator at room temperature
  2. filtrationThe catalyst was filtered off
  3. washwashed with MeOH
  4. additionDCM and 1 M K2CO3 were added
  5. customthe phases separated
  6. washThe organic layer was washed with brine
  7. customevaporated

Sources & evidence

ORD record
ord-18ca22394a7c499eb92b0772ef2ab1b3
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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