HCID 66731807, compound → HCID 66732323, compound

HRID 1963289Notes

Reaction equation

HRID 1963289 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:19]=[CH:18][CH:17]=[CH:16][C:4]=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:20][C:2]([F:1])([F:21])[C:3]1[CH:19]=[CH:18][CH:17]=[CH:16][C:4]=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 66731807HCID 66731807, compound

Product 1

HCID 66732323HCID 66732323, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalyst2×HCID 176Acetic AcidSolvent

Procedure

Methyl 2-(2-(trifluoromethyl)benzyl)isonicotinate (4.613 g, 15.62 mmol) was dissolved in acetic acid (40 mL) and platinum(IV) oxide (0.26 g, 1.14 mmol) added. The resulting mixture was hydrogenated in a Büchi hydrogenator for 3 h at room temperature and 5 bar. More platinum(IV) oxide (160 mg) was added and the hydrogenation continued at room temperature at 5 bar for 2 h. The catalyst was filtered off and washed with MeOH and the eluate evaporated. DCM and 10% K2CO3 were added and the phases separated. The water phase was extracted with DCM and the combined organic phase washed with water, passed through a phase separator and evaporated to yield methyl 2-(2-(trifluoromethyl)benzyl)-piperidine-4-carboxylate (4.20 g, 89%) as a yellow oil. MS m/z 302 (M+H)+

Workup

  1. waitthe hydrogenation continued at room temperature at 5 bar for 2 h
  2. filtrationThe catalyst was filtered off
  3. washwashed with MeOH
  4. additionDCM and 10% K2CO3 were added
  5. customthe phases separated
  6. extractionThe water phase was extracted with DCM
  7. washthe combined organic phase washed with water
  8. customevaporated

Sources & evidence

ORD record
ord-f13376e069a34f31ae9953fc613d8e20
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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