Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate → HCID 59180109, compound

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Reaction Steps

The title compound was synthesized in two steps. First, methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.5 g, 2.79 mmol) was reacted with 3,4-difluorophenylmagnesium bromide (14 mL, 7.0 mmol, 0.5 M in THF) according to General Procedure 3 to give methyl 4-(3,4-difluorophenyl)-1,6-dihydrocyclopenta[b]pyrrole-2-carboxylate, followed by hydrogenation according to General Procedure 6 (with 5% Pd/C), and was purified by column chromatography (Isco CombiFlash) eluting with a gradient of 0-30% EtOAc/heptane affording the title compound. 0.333 g. 1H NMR (400 MHz, ACETONE-d6) δ ppm 2.16-2.27 (m, 1H), 2.70-2.98 (m, 3H), 3.75 (s, 3H), 4.22 (t, J=7.22 Hz, 1H), 6.53 (d, J=1.85 Hz, 1H), 7.02-7.07 (m, 1H), 7.11 (ddd, J=11.96, 7.86, 2.15 Hz, 1H), 7.21 (dt, J=10.68, 8.43 Hz, 1H), 10.68 (br. s, 1H).

Provenance & Evidence