Diisopropylamine → HCID 86649625, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.855 ml of diisopropylamine in 15 ml of tetrahydrofuran was added 2.26 ml of a hexane solution containing 2.66 M n-butyllithium at 0° C., followed by stirring the reaction mixture at 0° C. for 30 minutes. After cooling down to −78° C., a solution of 1.54 g of 1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate in 5 ml of tetrahydrofuran was added to the reaction mixture, and the resultant mixture was stirred at −78° C. for 30 minutes. A solution of 1.00 g of 2-bromo-6-(bromomethyl)pyridine in 5 ml of tetrahydrofuran was added to the reaction mixture, followed by stirring the reaction mixture at −78° C. for 2 hours. To the reaction mixture was added saturated aqueous ammonium chloride solution, followed by extracting with ethyl acetate. The resulting ethyl acetate solution was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=20/1−2/1) to give the title compound as a yellow oil.

Provenance & Evidence