Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate → HCID 59180055, 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 3,5-difluorophenylmagnesium bromide (14 mL, 6.97 mmol, 0.5 M in THF, 2.5 equiv) according to General Procedure 3 to give methyl 4-(3,5-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 0-100% EtOAc/heptane afforded the title compound: 85 mg. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.27 (ddt, 1H), 2.73-3.00 (m, 3H), 3.84 (s, 3H), 4.17-4.23 (m, 1H), 6.60-6.67 (m, 2H), 6.69-6.75 (m, 2H), 9.01 (br. s, 1H) and 19F NMR (376 MHz, CHLOROFORM-d) δ ppm −110.76 (t, J=8.00 Hz).

Provenance & Evidence