Piperidine → HCID 86718521, compound

Participants

Reaction Steps

To a solution of benzyl((1R,2S)-1-hydroxy-1-(thiazol-2-yl)butan-2-yl)carbamate (330 mg, 1.077 mmol) in acetonitrile (25 mL) at 0° C. under argon was added piperidine (0.213 mL, 2.154 mmol) and dropwise iodotrimethylsilane (293 μL, 2.15 mmol) over a period of 5 minutes. Then, the reaction mixture was allowed to warm to room temperature and was stirred at room temperature for 2 hours. To the reaction mixture was added at 0° C. sodium thiosulfate (500 mg), followed by water (0.5 mL), and the reaction mixture was stirred vigorously at 0° C. for 15 minutes. Further 500 mg of sodium thiosulfate was added, and the mixture was diluted with EtOAc (50 mL), dried over Na2SO4, filtered and concentrated. The residue was triturated with EtOAc, filtered, and the filtrate was concentrated to give the title compound (250 mg, 67%) as a yellow oil.

Provenance & Evidence