Water → HCID 21186662, compound

Participants

Reaction Steps

In an atmosphere of argon, ethyl 9-hydroxy-2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate (1.04 g, 4.16 mmol) was dissolved in anhydrous THF (8.0 ml), and the solution was mixed with sodium hydride (182.3 mg, 4.56 mmol) at 0° C. This was stirred at the same temperature for 1 hour, mixed with methyl iodide (0.33 ml, 4.76 mmol) by its dropwise addition and then stirred at room temperature for 1.5 hours. The reaction solution was mixed with water and extracted with ethyl acetate, and the thus obtained organic layer was washed with water and saturated brine in that order and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (ether:hexane=1:1) to obtain the title compound (639.8 mg, 58.4%) as yellow oil.

Provenance & Evidence