(Diethylamino)sulfur trifluoride → 1-benzhydryl-3-fluoroazetidine

Participants

Reaction Steps

DAST (26.46 g, 0.164 mol) was added to a solution of Compound 19-2 (13.1 g, 0.0547 mol) in dry DCM (200 mL) at 0° C. The reaction mixture was stirred at room temperature overnight. The end of the reaction was monitored with TLC (petroleum ether/ethyl acetate=5:1). The reaction mixture was poured into ice water, extracted with DCM, washed with saturated brine, dried over anhydrous Na2SO4, and the organic layer was concentrated under reduced pressure, the resulting crude product was purified by column chromatography (petroleum ether/ethyl acetate=150:1) to give Compound 19-3 (4.0 g, 30% yield) as a white solid.

Provenance & Evidence