(Diethylamino)sulfur trifluoride → 8-Benzyl-6-fluoro-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one

Participants

Reaction Conditions

Reaction Steps

To a flask charged with DCM (5 mL) and a stir bar was added DAST (0.092 mL, 0.69 mmol) at −78° C., which was followed by addition of 8-benzyl-6-hydroxy-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one (I-35, Step C) (165 mg, 0.46 mmol) in DCM. The mixture was stirred at −78° C. for 15 minutes, and then allowed to warm up to RT slowly. The reaction was quenched with aq NaHCO3 and after 3 hours at RT it was extracted with DCM, dried over sodium sulfate, and purified by MPLC with hexane and EtOAc. Two spots were collected with the desired molecule weight in the ratio of 1:4. The less polar compound, which is the minor isomer, was designated as Isomer A, and the more polar major isomer was designated as Isomer B. LCMS: m/z 359 (M+H)+.

Provenance & Evidence