tert-butyl 4-(4,5-dimethyl-2-propionylphenyl)-3,6-dihydropyridine-1(2H)-carboxylate → Tert-butyl 4-(4,5-dimethyl-2-propionylphenyl)piperidine-1-carboxylate

HRID 29725Notes

Reaction equation

HRID 29725 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH:14]=2)=[C:4]([C:22](=[O:25])[CH2:23][CH3:24])[CH:3]=1>C(O)C.[Pd]>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:13][CH2:14]2)=[C:4]([C:22](=[O:25])[CH2:23][CH3:24])[CH:3]=1

Participants

4

Reactant 1

HCID 59788286tert-butyl 4-(4,5-dimethyl-2-propionylphenyl)-3,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 58660101Tert-butyl 4-(4,5-dimethyl-2-propionylphenyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of piperidine 84 (2.94 g, 8.5 mmol) and 10% Pd on carbon (144 mg, 0.65 mmol) in ethanol (10 mL) was hydrogenated at atmospheric pressure for approximately 2 h. The resulting mixture was filtered through a short plug of Celite®, eluting copiously with ethanol. The filtrate was concentrated in vacuo and the crude residue purified by flash chromatography on silica gel (gradient elution; 0%-25% EtOAc/hexanes as eluent) to afford 85 as a colorless oil.

Workup

  1. filtrationThe resulting mixture was filtered through a short plug of Celite®
  2. washeluting copiously with ethanol
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe crude residue purified by flash chromatography on silica gel (gradient elution; 0%-25% EtOAc/hexanes as eluent)

Sources & evidence

ORD record
ord-5f43325e8c6b4d18878e227562fc791f
Source dataset
uspto-grants-2008_09
Patent number
US07419990B2

Reaction notes

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