Xanthene-9-carboxylic acid → N-[9-(cyclooctylmethyl)-9-azabicyclo[3.3.1]nonan-3-yl]xanthene-9-carboxamide

Participants

Reaction Steps

15 ml of anhydrous N,N-dimethylformamide suspension having 165 mg of 3-amino-9-t-butoxycarbonyl-9-azabicyclo[3.3.1]nonane and 155 mg of xanthene-9-carboxylic acid was cooled with ice, and 224 mg of EDCI.HCl and 157 mg of 1-hydroxybenzotriazole were successively added thereto. The temperature was raised to room temperature immediately, and the reaction mixture was stirred for 21 hours. 10 ml of water was added to the reaction solution, followed by extraction with diethyl ether. The organic layer was washed with 10% citric acid solution, saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride, followed by drying over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and 301 mg of the title compound as a white solid was obtained.

Provenance & Evidence