Diisopropylamine → HCID 58285090, compound

Participants

Reaction Steps

6.52 g of diisopropylamine was dissolved in 24 mL of tetrahydrofuran, and the solution was cooled on ice. Then, 2.91 mL of n-butyl lithium (a 2.66 M hexane solution) was added thereto. After stirring at the same temperature for 30 minutes, the mixture was kept at −78° C. To the reaction mixture, 3.87 mL of trimethylsilyldiazomethane (a 2 M hexane solution) was added at the same temperature, and the mixture was stirred at the same temperature for 1 hour. To the reaction mixture, a solution prepared by dissolving 1 g of 1-tert-butylpyrimidin-4-one (synthesized by the method as described in J. Org. Chem., 2005, 70, 1930) in 6 mL of tetrahydrofuran was added at the same temperature, and the mixture was stirred at the same temperature for 1.5 hours, and heated overnight under reflux. To the reaction mixture, water was added, and the mixture was extracted with 200 mL of ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate. Then, the insolubles were filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in 120 mL of ethyl acetate, and 24 g of silica gel was added thereto at room temperature. The mixture was stirred at the same temperature for 1.5 hours. The insolubles were filtered, and the filtrate was concentrated under reduced pressure to obtain 830 mg of 1-tert-butylpiperidin-4-carboaldehyde [87-1] (hereinafter, referred to as the compound [87-1]).

Provenance & Evidence