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

HRID 270023Notes

Reaction equation

HRID 270023 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH:13]=2)=[CH:4][CH:3]=1>C(O)C.[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 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of Example 6B (2 g, 7.2 mmol) in ethanol (30 mL) was treated with 10% Pd/C (200 mg) and shaken at room temperature under 60 psi of H2 for 4 hours. The mixture was filtered and the filter cake was washed with ethanol. The filtrate was concentrated to provide the desired product (1.95 g, 96%). MS (CI) m/e 280 (M+H)+.

Workup

  1. filtrationThe mixture was filtered
  2. washthe filter cake was washed with ethanol
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-44e141fdc6db4e5a8e34394768a47651
Source dataset
uspto-grants-2008_11
Patent number
US07449485B2

Reaction notes

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