Triacetoxyperiodinane → 2'-(4-Methoxybenzyloxy)-4'-methyl-2,3,5,6-tetrahydro[1,3']bipyridinyl-4-one

Participants

Reaction Steps

A stirred solution of Dess-Martin periodinane (11.61 g, 27.37 mmol) in dichloromethane (122 ml) at room temperature was treated with a solution of 2′-(4-Methoxybenzyloxy)-4′-methyl-3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-4-ol (7.49 g, 22.81 mmol) in dichloromethane (81 ml) and the reaction mixture was stirred at room temperature. After 1 hour, the reaction mixture was washed with sat'd Na2S2O3(aq.), sat'd NaHCO3(aq.), and sat'd NaCl(aq.), dried over MgSO4, filtered, and concentrated. Elution through a flash column (silica gel 60, 230-400 mesh, 3:2 hexanes:EtOAc) gave the title compound as an off-white, crystalline solid (6.40 g, 86%).

Provenance & Evidence