Phthalimide → HCID 58833975, compound

Participants

Reaction Steps

Commercially available (S)-(−)-1-tert-butoxycarbonyl-2-pyrrolidinemethanol (1.00 g, 4.97 mmol) was dissolved in toluene (10 mL), and the mixture was stirred at room temperature for 1.5 hours after adding phthalimide (877 mg, 5.96 mmol), triphenylphosphine (1.96 g, 7.46 mmol), and diethyl azodicarboxylate (40% toluene solution, 3.4 mL, 7.46 mmol). The mixture was further stirred at 60° C. for 4 hours. Thereafter, water and ethyl acetate were added to separate the organic layer. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give (S)-2-[(1,3-dioxoisoindolin-2-yl)methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (1.88 g, quantitative).

Provenance & Evidence