Triethylamine → HCID 86664942, compound

Participants

Reaction Steps

7.2 ml (51.5 mmol) of triethylamine and then 5.9 g (15.5 mmol) of 4-(2-methylquinolin-4-ylmethoxy)-benzenesulfonyl chloride hydrochloride are added to a solution of 3.34 g (12.9 mmol) of methyl (R)-3-amino-2-piperidin-1-ylpropanoate dihydrochloride in 30 ml of dichloromethane and 30 ml of dimethylformamide cooled beforehand using an ice bath. The reaction medium is stirred at ambient temperature for 3 h 30, hydrolyzed, and then diluted with dichloromethane. The product is extracted with dichloromethane. The organic phase is washed with water, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue obtained is purified by chromatography on silica gel, elution being carried out with a 50/50 heptane/ethyl acetate mixture. 4 g (62%) of methyl (R)-3-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonylamino]-2-piperidin-1-ylpropanoate are obtained in the form of a white solid.

Provenance & Evidence