Hexane → HCID 68003934, compound

Participants

Reaction Steps

Under nitrogen atmosphere, 1.6M n-hexane solution of n-butyl lithium (65.6 ml) was added dropwise to a solution of 2,5-dibromo-3-picoline (25.1 g) in toluene (200 ml) at −78° C. and stirred at the same temperature for two hours. Next, a solution of 1-(tert-butoxycarbonyl)-4-piperidone (20.9 g) in toluene (200 ml) was added slowly dropwise. After the addition, the mixture was stirred at the same temperature for an hour. Then, the reaction solution was gradually warmed up to room temperature under stirring. After completion of the reaction, water was added and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) and the product was solidified with n-hexane to give 4-(5-bromo-3-methylpyridin-2-yl)-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (11.4 g) as a white solid.

Provenance & Evidence