6-Methyl-1-(2,2,2-trifluoroethyl)-5-(2,3,5-trifluorophenyl)pyridin-2(1H)-one → 6-Methyl-1-(2,2,2-trifluoroethyl)-5-(2,3,5-trifluorophenyl)piperidin-2-one

HRID 406566Notes

Reaction equation

HRID 406566 reaction equation
[CH3:1][C:2]1[N:7]([CH2:8][C:9]([F:12])([F:11])[F:10])[C:6](=[O:13])[CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[C:15]=1[F:22]>CO.[Pt](=O)=O>[CH3:1][CH:2]1[N:7]([CH2:8][C:9]([F:12])([F:10])[F:11])[C:6](=[O:13])[CH2:5][CH2:4][CH:3]1[C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[C:15]=1[F:22]

Participants

4

Reactant 1

HCID 866652086-Methyl-1-(2,2,2-trifluoroethyl)-5-(2,3,5-trifluorophenyl)pyridin-2(1H)-one

Product 1

HCID 866652096-Methyl-1-(2,2,2-trifluoroethyl)-5-(2,3,5-trifluorophenyl)piperidin-2-one

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A mixture of 6-methyl-1-(2,2,2-trifluoroethyl)-5-(2,3,5-trifluorophenyl)pyridin-2(1H)-one (3.73 g, 11.6 mmol) and platinum(IV) oxide (659 mg, 2.90 mmol) in MeOH (200 mL) was shaken on a Parr hydrogenation apparatus under an atmosphere of hydrogen (ca. 45 psi) for 2 h. The reaction mixture was filtered through a pad of Celite®, washing with MeOH, and the filtrate was concentrated in vacuo to give a crude solid. The crude product was purified by silica gel chromatography, eluting with a gradient of hexanes:Et2O—100:0 to 0:100, to give the title compound. MS: m/z=326.0 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite®
  2. washwashing with MeOH
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto give a crude solid
  5. customThe crude product was purified by silica gel chromatography
  6. washeluting with a gradient of hexanes

Sources & evidence

ORD record
ord-2e3b7e5ad19f4d1fa9d167a00b6a938b
Source dataset
uspto-grants-2014_06
Patent number
US08754096B2

Reaction notes

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