Tetrahydrofuran → HCID 67374271, compound

Participants

Reaction Steps

Under a nitrogen atmosphere and under ice-cooling, methyl magnesium bromide (20.7 mL, 0.97M tetrahydrofuran solution) was added dropwise into a tetrahydrofuran (50 mL) solution of (2R,5S)-5-(3,4,5-trifluorophenyl)pyrrolidine-1,2-dicarboxylic acid 1-t-butyl ester 2-ethyl ester (2.5 g). After stirring for 2 hours at the same temperature, ammonium chloride aqueous solution and ethyl acetate were added, and the organic layer was partitioned. The organic layer was washed with brine and was dried with magnesium sulfate, and the solvent was removed under a vacuum. Ethyl acetate (7 mL) and 4 N hydrochloric acid/ethyl acetate (20 mL) were added to the residue, and stirring was continued for 1 hour at room temperature. The solvent was removed under a vacuum, and ethyl acetate and sodium bicarbonate aqueous solution were added, and the organic layer was partitioned. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was removed under a vacuum, and the residue was purified by silica gel column chromatography (heptane/ethyl acetate→ethyl acetate), and the title compound (745 mg) was obtained. The physical property values are as follows.

Provenance & Evidence