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

Participants

Reaction Conditions

Reaction Steps

To 5 mL of an N,N-dimethylformamide suspension containing 0.50 g of 7-methoxy-4-methylquinolin-2(1H)-one, 0.11 g of 60% sodium hydride was added, and the mixture was stirred at 60° C. for 20 minutes. Thereto was added 1.09 g of 1-tert-butyl 4-ethyl 4-(3-((methanesulfonyl)oxy)propyl)piperidine-1,4-dicarboxylate, the temperature of the reaction mixture was increased to 70° C., and the reaction mixture was stirred for 4 hours. Thereto was added 0.11 g of 60% sodium hydride, and the resultant solution was stirred for 4 hours. Water and ethyl acetate were then 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 an aqueous 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 0.45 g of a yellow oily substance, 1-tert-butyl 4-ethyl 4-(3-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)propyl)piperidine-1,4-dicarboxylate.

Provenance & Evidence