Water → HCID 21186761, compound

Participants

Reaction Steps

In an atmosphere of argon, 3-pyridinemethanol (0.41 ml, 4.20 mmol) was dissolved in anhydrous THF (4.0 ml), and the solution was mixed with sodium hydride (173.6 mg, 4.34 mmol) at 0° C. and stirred at the same temperature for 1 hour. To this was added dropwise THF solution (4.0 ml) of ethyl 2-chloromethyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate (1.07 g, 3.98 mmol) at 0° C., and the mixture was stirred at from 0° C. to room temperature for 20 hours. The reaction solution was diluted with ethyl acetate, mixed with water and then extracted with ethyl acetate. Thethus obtainedorganiclayer was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (ethyl acetate:hexane=1:3—chloroform:methanol=40:1) to obtain the title compound (287.8 mg, 20.1%) as yellow oil.

Provenance & Evidence