Indole-3-Acetic Acid → Ethyl cis-4-[(1H-indol-3-ylacetyl)amino]-5-oxo-1-phenyl-3-pyrrolidinecarboxylate

Participants

Reaction Steps

To a solution of indole-3-acetic acid (248 mg, 1.42 mmol) in DMF (3 ml) was added 1,1-carbonyldiimidazole (230 mg, 1.42 mmol). After stirring for 2 h a solution of the aminopyrrolidinone of Example S (352 mg, 1.42 mmol) in DMF (1 ml) was added. After stirring for an additional 18 h the solvent was evaporated to give an oil which was chromatographed on silica gel eluting with EtOH/CH2Cl2 (2%-5%) to give 470 mg (91%) of the title compound as a solid. NMR (DMSO) 400 MHz : 3.25δ, m, 1H; 3.59δ, d, 2H; 3.88δ, t, 1H; 4.01δ, t, 1H; 4.65δ, q, 1H; 6.98δ, t, 1H; 7.08δ, t, 1H; 7.15δ, t, 1H; 7.24δ, d, 1H; 7.37, m, 3H; 7.56δ, d, 1H; 7.78δ, d, 2H; 8.62δ, d, 1H.

Provenance & Evidence