(Diethylamino)sulfur trifluoride → HCID 60067049, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of benzyl (3R,4R)-3-hydroxy-4-methoxypyrrolidine-1-carboxylate (0.818 g, 3.26 mmol) in 20 mL CH2Cl2 at −20° C. was added DAST (0.946 mL, 7.16 mmol). The reaction mixture was stirred at −20 ° C. and then room temperature overnight. The reaction mixture was quenched with 30 mL half saturated NaHCO3, stirred at room temperature for 15 min and extracted with EtOAc (2×30 mL). The organic layer was dried and concentrated. The residue was purified by flash column chromatography (25% EtOAc in Hexane) to give pale yellow solid (0.551 g, 67%). 1H NMR (CDCl3) δ 7.36-7.29 (5H, m), 5.13 (2H, s), 5.09, 4.92 (1H, m), 3.95-3.91 (1H, m), 3.74-3.35 (4H, m), 3.37 (3H, s).

Provenance & Evidence