HCID 66732272, compound → HCID 66732369, compound

HRID 1963294Notes

Reaction equation

HRID 1963294 reaction equation
[F:1][C:2]([F:22])([F:21])[O:3][C:4]1[CH:20]=[CH:19][C:7]([CH2:8][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:5]=1>C(O)(=O)C.[Pt](=O)=O>[F:21][C:2]([F:1])([F:22])[O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH:9]2[CH2:10][CH:11]([C:12]([O:14][CH3:15])=[O:13])[CH2:16][CH2:17][NH:18]2)=[CH:19][CH:20]=1

Participants

4

Reactant 1

HCID 66732272HCID 66732272, compound

Product 1

HCID 66732369HCID 66732369, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of methyl 2-(4-(trifluoromethoxy)benzyl)isonicotinate (8.04 g, 25.83 mmol) in acetic acid (40 mL) was added platinum(IV) oxide (0.343 g, 1.51 mmol) and the resulting mixture hydrogenated at 5 bar in a Büchi hydrogenator for 5 h. The reaction mixture was filtered through a diatomeous earth filter carton and the catalyst washed with methanol. The solvents were evaporated, the residue dissolved in DCM and washed with 10% Na2CO3. After phase separation the aqueous layer was extracted with DCM. The combined organic layers were dried over MgSO4 and evaporated. Methyl 2-(4-(trifluoromethoxy)benzyl)piperidine-4-carboxylate (8.19 g, 100%) was isolated as a dark brown oil. MS m/z 318 (M+H)+

Workup

  1. filtrationThe reaction mixture was filtered through a diatomeous earth
  2. filtrationfilter carton
  3. washthe catalyst washed with methanol
  4. customThe solvents were evaporated
  5. dissolutionthe residue dissolved in DCM
  6. washwashed with 10% Na2CO3
  7. customAfter phase separation the aqueous layer
  8. extractionwas extracted with DCM
  9. dry with materialThe combined organic layers were dried over MgSO4
  10. customevaporated

Sources & evidence

ORD record
ord-3df65667d29247c39489dd176e71b820
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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