Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate → HCID 59180218, compound

Participants

Reaction Steps

The title compound was synthesized in two steps. First, methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.64 g, 3.6 mmol) and (4-benzylphenyl)magnesium bromide were reacted according to General Procedure 3 to give methyl 4-(4-benzylphenyl)-1,6-dihydrocyclopenta[b]pyrrole-2-carboxylate. (4-Benzylphenyl)magnesium bromide was synthesized from 1-benzyl-4-bromobenzene. (In an inert Ar atmosphere, to a suspension of Mg (0.44 g, 18.2 mmol) turnings in 50 mL of THF was added very slowly (dropwise) 1-benzyl-4-bromobenzene, then catalytic amount of iodine was added. The reaction mixture was stirred for 30 min at room temperature, then 25 mL of THF was added and the mixture was stirred for 3 hours at 75-80° C. (gentle reflux of THF).) The methyl 4-(4-benzylphenyl)-1,6-dihydrocyclopenta[b]pyrrole-2-carboxylate was hydrogenated according to General Procedure 6 with 5% Pd/C and a hydrogen balloon, and was purified by column chromatography (Isco CombiFlash) eluting with a gradient of 0-100% EtOAc/heptane to afford the title compound. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.23-2.35 (m, 1H), 2.71-2.97 (m, 3H), 3.82 (s, 3H), 3.96 (s, 2H), 4.20 (t, J=7.32 Hz, 1H), 6.63 (d, J=1.76 Hz, 1H), 7.09-7.15 (m, 5H), 7.16-7.23 (m, 2H), 7.28-7.32 (m, 2H), 8.84 (br. s, 1H).

Provenance & Evidence