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

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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 1 M Na2CO3-sol. and extracted twice with dichloromethane. The organic layers were washed with diluted NaHSO3 solution and brine, dried over Na2SO4, 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, 5.14 mmol, 78.3%) as a dark green solid. MS (ISP): m/z=159.1 [(M+H)+].

Provenance & Evidence