HCID 118483541, compound → Tert-butyl 4-(3,5-difluoro-2-(trifluoromethyl)phenyl)piperidine-1-carboxylate

HRID 58435Notes

Reaction equation

HRID 58435 reaction equation
[F:1][C:2]1[C:3]([C:22]([F:25])([F:24])[F:23])=[C:4]([C:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1>CCO.[Pd]>[F:1][C:2]1[C:3]([C:22]([F:24])([F:25])[F:23])=[C:4]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 1

HCID 118483541HCID 118483541, compound

Product 1

HCID 118483534Tert-butyl 4-(3,5-difluoro-2-(trifluoromethyl)phenyl)piperidine-1-carboxylateYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of tert-butyl 4-(3,5-difluoro-2-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (26, 0.750 g, 2.11 mmol) and 10% Pd/C (1.0 g) in EtOH (50 mL) stirred at ambient temperature under an atmosphere of H2 for 24 h. The mixture was filtered through Celite and the filtrate concentrated under reduced pressure to afford tert-butyl 4-(3,5-difluoro-2-(trifluoromethyl)phenyl)piperidine-1-carboxylate (27) as a white solid (535 mg, 82%). 1H NMR (300 MHz, CDCl3) δ 6.97-6.85 (m, 1H), 6.85-6.69 (m, 1H), 4.37-4.16 (m, 2H), 3.23-3.05 (m, 2H), 2.89-2.71 (m, 2H), 1.86-1.51 (m, 4H), 1.48 (s, 9H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-7708858b12ac41e399d3c96c936fcd56
Source dataset
uspto-grants-2016_09
Patent number
US09434727B2

Reaction notes

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