Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate → HCID 59180131, 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 (447 mg, 2.5 mmol) was reacted with 3-methoxybenzylmagnesium bromide (0.25 M in hexanes, (25 mL, 6.3 mmol) according to General Procedure 3. The resulting exo-olefin ((E)-methyl 4-(3-methoxybenzylidene)-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 chromatography, eluting with heptane-EtOAc, gradient 0 to 40% EtOAc to afford the title compound. 155 mg. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.04-2.21 (m, 1H) 2.50-2.63 (m, 1H) 2.62-2.71 (m, 2H) 2.72-2.86 (m, 2H) 3.23-3.36 (m, 1H) 3.81 (s, 6H) 6.44 (d, J=1.56 Hz, 1H) 6.72-6.85 (m, 3H) 7.22 (t, J=7.78 Hz, 1H) 8.76 (br. s, 1H).

Provenance & Evidence