Methyl 2-(piperidin-1-yl)pyridine-4-carboxylate → [2-(Piperidin-1-yl)pyridin-4-yl]methanol

Participants

Reaction Steps

To a suspension of LAH (5.5 g, 0.145 mol) in dry THF (500 mL) at 0° C. was added methyl 2-piperidin-1-ylisonicotinate (18 g, 0.095 mol) in dry THF (100 mL) under N2 atmosphere. The reaction mixture was stirred at RT for 4 h and quenched with 10% aqueous NaOH solution at −20° C. The solid was filtered off, washed with THF and concentrated. The residue was dissolved in CH2Cl2 (250 mL), washed with water, brine and dried. The solvent was removed under vacuum and the crude was purified by column chromatography over silica gel (CHCl3/MeOH, 9:1) to give (2-piperidin-1-yl pyridin-4-yl)methanol (12 g, 65%). 1H NMR (DMSO-d6) δ 7.98 (d, J=5.2 Hz, 1H), 6.71 (s, 1H), 6.51 (br d, 1H), 5.24 (t, J=5.2 Hz, 1H), 4.41 (d, J=5.2 Hz, 2H), 3.49-3.46 (m, 4H), 1.58-1.50 (m, 6H).

Provenance & Evidence