Sodium Carbonate → 6,7-Dihydro-7-oxo-5H-cyclopenta[b]pyridine-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 7-hydroxy-6,7-dihydro-5H-[1]pyrindine-3-carbonitrile (1.05 g, 6.56 mmol) in dichloromethane (50 ml) at 0° C. was added Dess-Martin periodinane (2.92 g, 6.88 mmol) and the mixture was stirred at 23° C. for 2 hours. Poured on a solution of sodium carbonate (1M) and extracted twice with dichloromethane. The organic layers were washed with a diluted solution of sodium hydrogensulfite and brine, dried over sodium sulphate, filtered and evaporated to give a grey solid. The residue was purified by silica gel flash chromatography with n-heptane/ethyl acetate to give the 7-oxo-6,7-dihydro-5H-[1]pyrindine-3-carbonitrile (855 mg, 78%) as a dark green solid. MS (ISP): m/z=159.1 [M+H]+.

Provenance & Evidence