trans-N-Boc-2-(1-isohexenyl)-6-methylpiperidine → trans-N-Boc-2-isohexyl-6-methylpiperidine
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
Product 1
Reagents, catalysts & solvents 2
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) δ3.92-3.90 (m, 1 H), 3.79-3.76 (m, 1 H), 1.84-1.14 (m, 28 H), 0.87-0.82 (d, 6 H); 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.