Boron tribromide → HCID 57970104, compound

Participants

Reaction Steps

A solution of (S)-(1-(4-chlorophenyl)cyclobutyl)-(3-(6-methoxy-4-methylquinolin-2-ylamino)pyrrolidin-1-yl)methanone (0.60 g) in dichloromethane (50 mL) was cooled to −78° C., followed by addition of a solution of 1 M boron tribromide in dichloromethane (7.3 mL), and the mixture was stirred for 12 h while slowly heating to room temperature. To the reaction mixture was added a saturated sodium hydrogencarbonate solution to make it basic, and 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 and concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (silica gel, chloroform/methanol, and NH silica gel, chloroform/methanol) and crystallized with ethyl acetate to obtain white solid (S)-(1-(4-chlorophenyl)cyclobutyl)-(3-(6-hydroxy-4-methylquinolin-2-ylamino)pyrrolidin-1-yl)methanone (0.278 g).

Provenance & Evidence