1,1'-Carbonyldiimidazole → HCID 44302614, compound

Participants

Reaction Steps

To a solution of trans-3-carboxy-4-(3-cyclopentoxy-4-methoxyphenyl)-1-(methoxycarbonyl)pyrrolidine (1.5 g, 4.1 mmol) in 11 mL of CH2Cl2 at 0° C. was added 1,1'-carbonyldiimidazole (736 mg, 4.5 mmol) in portions. The cooling bath was removed, and the solution was stirred at room temperature for 20 min. Ammonia gas was passed over the stirring solution for 4 min, and stirring was continued an additional 15 min. The solution was diluted with CH2Cl2 and poured into 1M H3PO4. The aqueous layer was extracted with CH2Cl2 (2×), and the combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure to a pale yellow foam. Silica gel chromatography (8:1:1, CH2Cl2 :ethyl acetate:methanol) provided trans-3-aminocarbonyl-4-(3-cyclopentoxy-4-methoxyphenyl)-I-(methoxycarbonyl)pyrrolidine as a white solid (1.1 g, 76%), m.p. 130°-32° C. Anal. Calcd for C19H26N2O5 : C, 62.97; H, 7.23; N, 7.73. Found: C, 63.03; H, 7.28; N, 7.65.

Provenance & Evidence