4-Nitrophenyl chloroformate → HCID 18712733, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (±)-2,2-dimethyl-3-(3,4-difluorophenyl)-5-oxo-morpholine (240 mg, 0.996 mmol) in THF (10 mL) at −78° C. was added lithium bis(trimethylsilyl)amide (1.10 mL, 1.0 M in THF). The mixture was stirred for 30 min at 0° C. and then cooled back to −78° C. The mixture was transferred via a cannula to a precooled solution of 4-nitrophenyl chloroformate (605 mg, 3.0 mmol) in THF (10 mL) at −78° C. The resulting mixture was stirred while warmed to room temperature over 3 hours. The reaction was quenched with water (2 mL) and extracted with EtOAc (2×100 mL). The organic layer was dried with Na2SO4 and the solvent was evaporated. The residue was purified by column chromatography (SiO2, 40:60 EtOAc/Hexanes) to afford 0.328 g (81%) of the product as a pale oil.

Provenance & Evidence