HCID 66732066, compound → HCID 66732410, compound

HRID 1963278Notes

Reaction equation

HRID 1963278 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:19]=[CH:18][C:6]([CH2:7][C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][N:17]=2)[C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1>C(O)(=O)C.CO.[Pt](=O)=O>[F:21][C:2]([F:1])([F:20])[C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH:8]2[CH2:9][CH:10]([C:11]([O:13][CH3:14])=[O:12])[CH2:15][CH2:16][NH:17]2)=[CH:18][CH:19]=1

Participants

5

Reactant 1

HCID 66732066HCID 66732066, compound

Product 1

HCID 66732410HCID 66732410, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalyst2×HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

Methyl 2-(4-(trifluoromethyl)benzyl)isonicotinate (11.5 g, 38.95 mmol) was dissolved in acetic acid (200 mL) and methanol (100 mL). Platinum(IV) oxide (0.177 g, 0.78 mmol) was added and the mixture hydrogenated in a Büchi hydrogenator at room temperature and 7 bar for 6 h. The catalyst was filtered off. Fresh platinum(IV) oxide (0.18 g, 0.78 mmol) was added and hydrogenation continued at 9 bar for 7 h. The catalyst was filtered off, the solvent was evaporated and the residue partitioned between ethyl acetate and Na2CO3 (aq). The organic layer was dried over MgSO4, filtered through celite and the solvent evaporated. Methyl 2-(4-(trifluoromethyl)benzyl)piperidine-4-carboxylate (9.5 g, 81%) was isolated.

Workup

  1. customhydrogenated in a Büchi hydrogenator at room temperature
  2. filtrationThe catalyst was filtered off
  3. waithydrogenation continued at 9 bar for 7 h
  4. filtrationThe catalyst was filtered off
  5. customthe solvent was evaporated
  6. customthe residue partitioned between ethyl acetate and Na2CO3 (aq)
  7. dry with materialThe organic layer was dried over MgSO4
  8. filtrationfiltered through celite
  9. customthe solvent evaporated

Sources & evidence

ORD record
ord-ace34b0d4fec457a815bba4ef3f4cf8f
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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