Citric Acid → 2-(Pyrrolidine-1-carbonyl)-hexahydro-cyclopenta[c]pyrrol-5-one

Participants

Reaction Steps

Hexahydro-cyclopenta[c]pyrrol-5-one trifluoroacetate 1f (478 mg, 2 mmol) was dissolved in 20 mL of dichloromethane followed by addition of pyrrolidine-1-carbonyl chloride (0.276 mL, 2.5 mmol) and triethylamine (0.84 mL, 6 mmol). The reaction mixture was reacted overnight at room temperature. The mixture was adjusted to pH 4 with a solution of 10% citric acid. The mixture was extracted with dichloromethane (50 mL×3). The combined organic extracts were washed with 50 mL of saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 2-(pyrrolidine-1-carbonyl)-hexahydro-cyclopenta[c]pyrrol-5-one 8a (0.26 g, yield 58.5%) as a colorless oil.

Provenance & Evidence