1,1'-Carbonyldiimidazole → HCID 57692649, compound

Participants

Reaction Steps

To a solution of (2S,4R)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate (500 mg, 2.04 mmol) in dry THF (6 mL) was added CDI (430 mg, 2.65 mmol) in one portion and the mixture was stirred at rt for 6 h. The amine, 4-chloroisoindoline hydrochloride (0.89 g, 4.7 mmol) was then added in portions, followed by slow addition of DIEA (1.07 mL, 6.12 mmol). The reaction was stirred at rt for overnight. The reaction was diluted with 120 mL EtOAc, washed with 1N HCl (2×50 mL), water and brine (50 mL each), and dried over Na2SO4 and concentrated down to a thick brownish oil. The crude was purified by silica chromatography (eluent=hexanes/EtOAc 2:1), giving the ester product, (2S,4R)-1-tert-butyl 2-methyl 4-(4-chloroisoindoline-2-carbonyloxy)pyrrolidine-1,2-dicarboxylate, as a light pinkish foamy solid (0.79 g, 91% yield).

Provenance & Evidence