Boron tribromide → HCID 57970109, compound

Participants

Reaction Steps

A solution of (S)-1-(4-chlorophenyl)-2-(3-(6-methoxy-4-methylquinolin-2-ylamino)pyrrolidin-1-yl)ethane-1,2-dione (0.467 g) in dichloromethane (50 mL) was cooled to −78° C., followed by addition of a solution (6.1 mL) of 1 M boron tribromide in dichloromethane, and the mixture was stirred for 3 h while heating slowly to room temperature. To the reaction mixture was added a saturated sodium hydrogencarbonate solution to make it basic, and then the mixture was extracted with chloroform. The aqueous layer was reextracted with a mixed solution of ethyl acetate and n-butanol, then the organic layer was combined, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (silica gel, chloroform/methanol, and NH silica gel, chloroform/methanol) to obtain light yellow amorphous (S)-1-(4-chlorophenyl)-2-(3-(6-hydroxy-4-methylquinolin-2-ylamino)pyrrolidin-1-yl)ethane-1,2-dione (0.068 g).

Provenance & Evidence