Triethylamine → ethyl 4-({[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]carbonyl}amino)benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 181 mg of the crude tert-butyl[(1R)-1-(1-naphthyl)ethyl][(3-phenylpiperidin-4-yl)methyl]carbamate and 0.114 mL of triethylamine and 2.7 mL of THF was added 117 mg of ethyl 4-isocyanatobenzoate at room temperature. The reaction vessel was tightly sealed, followed by stirring at 100° C. overnight. The reaction mixture was cooled to room temperature, and a saturated aqueous sodium hydrogen carbonate solution was then added thereto, followed by extraction with chloroform. Then, the organic layer was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain 357 mg of ethyl 4-({[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]carbonyl}amino)benzoate as a crude product. ESI+: 636

Provenance & Evidence