Triethylamine → N-[(2E)-2-(1,2,6,7-tetrahydro-8H-cyclopenta[b]furo[3,2-d]pyridin-8-ylidene)ethyl]propanamide

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Reaction Steps

To a mixture of (2E)-2-(1,2,6,7-tetrahydro-8H-cyclopenta[b]furo[3,2-d]pyridin-8-ylidene)ethanamine (220 mg, 0.999 mmol) and triethylamine (167 μL, 1.20 mmol) in dichloromethane (10 mL) was added propionyl chloride (104 μL, 1.20 mmol) under ice-cooling, and the mixture was stirred for 10 min. The reaction solution was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate=0/100→10/90) and recrystallization (chloroform/hexane) to give the title compound (195 mg, yield 75%).

Provenance & Evidence