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

Participants

Reaction Steps

A stirred solution of Dess-Martin periodinane (9.19 g, 21.67 mmol) in dichloromethane (95 ml) at room temperature was treated with a solution of 2′-(4-Methoxybenzyloxy)-3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-4-ol (5.68 g, 18.06 mmol) in dichloromethane (60 ml) and the reaction mixture was stirred at room temperature (a mild exotherm was observed). After 1 hour, the reaction mixture was washed with sat'd Na2S2O3(aq.), sat'd NaHCO3(aq.), sat'd NaCl(aq.), dried over MgSO4, filtered, and concentrated. Elution through a flash column (silica gel 60, 230-400 mesh, 7:3 hexanes:EtOAc to 3:2 hexanes:EtOAc) gave the title compound as a yellow, viscous oil (4.01 g, 71%).

Provenance & Evidence