Dimethylformamide → 1-tert-butyl 4-ethyl 4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-1,4-dicarboxylate

Participants

Reaction Conditions

Reaction Steps

To 7 mL of an N,N-dimethylformamide solution containing 0.64 g of 7-methoxyquinolin-2(1H)-one, 0.15 g of 60% sodium hydride was added at room temperature, and the mixture was stirred at 60° C. for 20 minutes. Thereto was added 1.50 g of 1-tert-butyl 4-ethyl 4-(3-((methanesulfonyl)oxy)propyl)piperidine-1,4-dicarboxylate, the mixture was stirred at 70 to 80° C. for 1 hour and 30 minutes, and thereto was further added 75 mg of 60% sodium hydride, and the mixture was stirred for 2 hours and 30 minutes. The reaction mixture was cooled to room temperature, and then ethyl acetate and water were added thereto. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with a saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=1:1] to obtain 0.72 g of a yellow oily substance, 1-tert-butyl 4-ethyl 4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-1,4-dicarboxylate.

Provenance & Evidence