3,3-Diphenylpropylamine → 4-[4-(3,5-Dichlorophenyl)-2,6-dimethyl-5-(3,3-diphenylpropylcarbamoyl)pyridine-3-carbonyl]piperazine-1-carboxylic acid t-butyl ester

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Reaction Steps

300 mg (0.588 mmol) of 4-[5-carboxy-4-(3,5-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3-carbonyl] piperazine-1-carboxylic acid t-butyl ester, 0.12 ml (0.882 mmol) of 3,3-diphenylpropylamine and 248 mg (1.29 mmol) of WSC hydrochloride were stirred in 15 ml of dichloromethane and 1 ml of DMF at room temperature overnight. After dichloromethane was evaporated under reduced pressure, ethyl acetate was added. After being washed with saturated aqueous sodium hydrogencarbonate solution and 1 N hydrochloric acid, the organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was dissolved in 8 ml of acetone. 811 mg (1.48 mmol) of diammonium cerium nitrate (IV) suspended in 8 ml of water was dropped and stirred at room temperature for 1 hour. After acetone was evaporated under reduced pressure, ethyl acetate was added. After being washed with water, the organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (dichloromethane/methanol=100/1 to 80/1) to obtain the title compound.

Provenance & Evidence