6-Hydroxy-3,4-dihydro-2(1H)-quinolinone → 6-(1-cyclobutylpiperidin-4-yloxy)-3,4-dihydroquinolin-2(1H)-one

Participants

Reaction Steps

Under a nitrogen atmosphere, to a solution of 6-hydroxy-3,4-dihydroquinolin-2(1H)-one (5.00 g) and N-cyclobutyl-4-hydroxypiperidine (which can be synthesized as described in WO2005/108384) (7.10 g) in tetrahydrofuran (50 mL), diethyl azodicarboxylate (40% in toluene, 16.7 mL) was added dropwise under ice cooling. After completion of the dropwise addition, the reaction mixture was warmed to room temperature and stirred for 40 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluting solvent: chloroform/methanol=95/5) to give the titled compound (2.30 g, 25%) as a colorless powder.

Provenance & Evidence