(Diethylamino)sulfur trifluoride → HCID 86707498, compound

Participants

Reaction Steps

To a solution of (3S,4R)-4-azido-1-((R)-1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl)pyrrolidin-3-ol (2.4 g, 7.5 mmol) in dichloromethane (30 mL) at −78° C., was added diethylaminosulfur trifluoride (1.17 mL, 8.95 mmol). The resulting solution was allowed to warm to ambient temperature and stirred overnight. The mixture was concentrated under reduced pressure and the residue was dissolved in ethyl acetate and washed with water and brine, then dried (MgSO4), filtered and concentrated. The crude residue was purified by column chromatography (Biotage, 40M; 10-25% ethyl acetate/hexanes gradient) to afford 5-((1R)-1-((3R)-3-azido-4-fluoropyrrolidin-1-yl)-2,2,2-trifluoroethyl)-2-chloropyridine (1.02 g, 42%).

Provenance & Evidence