1,1'-Carbonyldiimidazole → 1-t-Butyl 2-methyl (2S,4R)-4-{[(4-vinyl-1,3-dihydro-2H-isoindol-2-yl)carbonyl]oxy}pyrrolidine-1,2-dicarboxylate

Participants

Reaction Steps

A solution of 1-t-butyl 2-methyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate (10.1 g, 41.4 mmol) in DMF (90 mL) under nitrogen was cooled to 0° C. Solid 1,1′-carbonyldiimidazole (6.70 g, 41.4 mmol) was added, and the reaction mixture was warmed to RT. After 2 hours, a solution of 4-vinylisoindoline (6.00 g, 41.4 mmol) in DMF (10 mL) was added. The mixture was then heated in a 60° C. oil bath for 2 hours, cooled to RT and poured into water and 5% potassium bisulfate. The resulting mixture was extracted with EtOAc (4×250 mL). The combined organic phases were washed with brine and dried over Na2SO4; and the solvent was evaporated. Flash column chromatography (hexane/EtOAc 70/30) gave the title compound as a white foam, 13.9 g. LRMS (ESI) m/z 417 [(M+H)+; calcd for C27H29N2O6: 417].

Provenance & Evidence