trans-N-Boc-2-(1-isohexenyl)-6-methylpiperidine → trans-N-Boc-2-isohexyl-6-methylpiperidine

HRID 1919733Notes

Reaction equation

HRID 1919733 reaction equation
[C:1]([N:8]1[C@@H:13]([CH3:14])[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH:15]=[CH:16][CH2:17][CH:18]([CH3:20])[CH3:19])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>C(O)C.[Pd]>[C:1]([N:8]1[C@@H:13]([CH3:14])[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2]

Participants

4

Reactant 1

HCID 86596523trans-N-Boc-2-(1-isohexenyl)-6-methylpiperidine

Product 1

HCID 67499496trans-N-Boc-2-isohexyl-6-methylpiperidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of trans-N-Boc-2-(1-isohexenyl)-6-methylpiperidine (1.35, 4.79 mmol) in 4 mL of ethanol was shaken under 58 psi of H2 pressure over 0.34 g Pd/C catalyst overnight, and then the mixture was filtered through Celite and concentrated to give 1.40 g (quantitative) of the product. No further purification was necessary. 1H NMR (250 MHz) δ 3.92-3.90 (m, 1H), 3.79-3.76 (m, 1H), 1.84-1.14 (m, 28H), 0.87-0.82 (d, 6H); 13C NMR (62.7 MHz) 154.7, 78.6, 51.6, 46.9, 38.9, 34.5, 28.5, 27.9, 26.8, 24.8, 23.2, 22.6, 22.5, 20.8, 13.7 ppm.

Workup

  1. filtrationthe mixture was filtered through Celite
  2. concentrationconcentrated
  3. customto give 1.40 g (quantitative) of the product
  4. customNo further purification

Sources & evidence

ORD record
ord-d547ddf44b9048fca6655cb883761ced
Source dataset
uspto-grants-2012_05
Patent number
US08168657B2

Reaction notes

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