HCID 66731965, compound → HCID 66731845, compound

HRID 1963327Notes

Reaction equation

HRID 1963327 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=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:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([C:19]([F:22])([F:20])[F:21])[CH:18]=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 66731965HCID 66731965, compound

Product 1

HCID 66731845HCID 66731845, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of methyl 2-(3-fluoro-5-(trifluoromethyl)benzyl)isonicotinate (4.5 g, 14.37 mmol) in acetic acid (50 mL) was added platinum(IV) oxide (0.36 g, 1.59 mmol) and the resulting mixture hydrogenated at 5 bar in a Büchi hydrogenator for 3 h 45 min. 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-(3-fluoro-5-(trifluoro-methyl)benzyl)piperidine-4-carboxylate (4.11 g, 90%) was isolated as a pale yellow oil that partially solidified upon standing. MS m/z 320 (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-8f012636d36d41ed8a8e4fee60da93d9
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

Loading…