Diisopropylamine → HCID 58097102, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.11 ml of diisopropylamine in 20 ml of tetrahydrofuran was added 0.73 ml of a hexane solution containing 2.66 M n-butyl lithium at −78° C. The reaction mixture was warmed to 0° C., and then cooled to −78° C. 1.2 ml of 2-bromo-6-methylpyridine was slowly added to the reaction mixture below −70° C., followed by stirring the reaction mixture at −78° C. for 30 minutes. 1.95 g of cerium(III) chloride was added to the reaction mixture at −78° C., followed by stirring the reaction mixture at −78° C. for 1 hour. 0.98 ml of 1-benzyl-4-piperidone was slowly added to the reaction mixture below −70° C., followed by stirring the reaction mixture at −78° C. for 1 h. To the reaction mixture was added saturated aqueous ammonium chloride solution, followed by adding ethyl acetate. An insoluble matter was filtered off using Celite. The organic layer was separated, washed with water and brine, dried over anhydrous magnesium sulfate, and filtered.

Provenance & Evidence