(S)-2-(2-isopropoxy-3-methylphenyl)-1-(4-pyridinyl)ethanol → (S)-2-(2-isopropoxy-3-methylphenyl)-1-(4-piperidinyl)ethanol
Reaction equation
[CH:1]([O:4][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:12][C@@H:13]([C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)[OH:14])([CH3:3])[CH3:2]>O=[Pt]=O.CC(O)=O>[CH:1]([O:4][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:12][C@@H:13]([CH:15]1[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]1)[OH:14])([CH3:3])[CH3:2]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Shake a mixture of (S)-2-(2-isopropoxy-3-methylphenyl)-1-(4-pyridinyl)ethanol (21.1 g, 78 mmol), HOAc (400 mL) and PtO2 (370 mg) with H2 (50 psi) for 15 hr. Filter the mixture through celite and evaporate the solvent to give (S)-2-(2-isopropoxy-3-methylphenyl)-1-(4-piperidinyl)ethanol as the acetate salt; 1H-NMR (CDCl3) δ 7.1-6.9 (m, 2H), 4.2 (m, 1H), 3.6 (m, 1H), 3.4 (m, 2H), 2.9-2.7 (m, 4H), 2.3 (s, 3H), 2.0 (s, 3H), 2.1-1.5 (m, 5H), 1.3 (d, 6H).