Acetonitrile → HCID 69053957, compound

Participants

Reaction Steps

47.7 ml (85.9 mmol) of 1.8 M lithium diisopropylamide-n-heptane/tetrahydrofuran/ethylbenzene solution was added to 50 ml of tetrahydrofuran and 4.14 ml (79.3 mmol) of acetonitrile was added dropwise under cooling with a dry ice-acetone bath, and the reaction solution was stirred for 3.0 hours. Under the same conditions, a solution of 13.9 g (66.1 mmol) of 4-cyanopiperidin-1-carboxylic acid tert-butyl ester in 30 ml of tetrahydrofuran was further added dropwise and then the reaction solution was stirred for 24 hours while the temperature of the reaction solution was slowly raised to room temperature. After completion of the reaction, ice water was added to the reaction solution and the reaction solution was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride aqueous solution and then dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was subjected to silica gel column chromatography [n-hexane/ethyl acetate=90/10-50/50 (V/V)], and the fraction including the desired compound was concentrated under reduced pressure to provide 10.7 g of the title compound as a yellow oil (yield: 64%).

Provenance & Evidence