1,1-Dimethylethyl 4-(4-fluorophenyl)-3,6-dihydro-1(2H)-pyridinecarboxylate → Tert-butyl 4-(4-fluorophenyl)piperidine-1-carboxylate

HRID 509271Notes

Reaction equation

HRID 509271 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]=2)=[CH:4][CH:3]=1>CCO.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 157514261,1-Dimethylethyl 4-(4-fluorophenyl)-3,6-dihydro-1(2H)-pyridinecarboxylate

Product 1

HCID 11312007Tert-butyl 4-(4-fluorophenyl)piperidine-1-carboxylateYield 95.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Tert-butyl 4-(4-fluorophenyl)-5,6-dihydropyridine-1(2H)-carboxylate (48 mg, 0.173 mmol) was dissolved in EtOH (2 ml), followed by addition of Pd (10 wt % on activated carbon, 5 mg), and then the resulting liquid was stirred at room temperature under hydrogen stream for 2 hours. The resulting reaction liquid was filtered, concentrated under reduced pressure, and dried under vacuum, to obtain 46 mg of colorless oil (95%).

Workup

  1. customThe resulting reaction liquid
  2. filtrationwas filtered
  3. concentrationconcentrated under reduced pressure
  4. customdried under vacuum

Sources & evidence

ORD record
ord-1651caeaaf0945a8ac476c9e1dcd88e0
Source dataset
uspto-grants-2015_08
Patent number
US09096571B2

Reaction notes

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