methyl 2-[(E)-2-phenylvinyl]isonicotinate → Methyl 2-(2-cyclohexylethyl)piperidine-4-carboxylate

Reaction equation

[C:1]1(/[CH:7]=[CH:8]/[C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][N:18]=2)[C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>Cl.CO.[Pt]=O>[CH:1]1([CH2:7][CH2:8][CH:9]2[CH2:10][CH:11]([C:12]([O:14][CH3:15])=[O:13])[CH2:16][CH2:17][NH:18]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Procedure

To a solution of methyl 2-[(E)-2-phenylvinyl]isonicotinate in hydrochloric acid and MeOH was added platinum oxide, followed by stirring at room temperature for 8 hours under a hydrogen atmosphere of 3 atm. The reaction mixture was filtered through Celite, and the filtrate was then concentrated under reduced pressure. To the residue were added an aqueous Na2CO3 solution and xylene, and the aqueous layer was extracted with CHCl3. The organic layer was dried over MgSO4 and then concentrated under reduced pressure to obtain methyl 2-(2-cyclohexylethyl)piperidine-4-carboxylate as a colorless oily substance.