Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate → HCID 59180231, 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 (0.50 g, 2.8 mmol) was reacted with 3,4-dimethoxy-benzylmagnesium chloride (0.25 M in THF, 28.0 mL, 7.0 mmol) according to General Procedure 3. The resulting exo-olefin ((E)-methyl 4-(3,4-dimethoxybenzylidene)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate) was then converted to the title compound by hydrogenation according to General Procedure 6 (with 5% Pd/C). The crude product was purified by column chromatography (Isco CombiFlash) eluting with a gradient of 0-50% EtOAc/heptane to afford the title compound: 0.050 g. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.06-2.18 (m, 1H) 2.50-2.68 (m, 3H) 2.68-2.81 (m, 2H) 3.20-3.35 (m, 1H) 3.74-3.94 (m, 9H) 6.36-6.46 (m, 1H) 6.69 (d, J=1.76 Hz, 1H) 6.74 (dd, J=8.10, 1.56 Hz, 1H) 6.82 (d, J=8.10 Hz, 1H) 8.80 (br. s, 1H).

Provenance & Evidence