Methyl 6-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate → Methyl 6-(3-methoxybenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

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Reaction Steps

The title compound was synthesized in two steps. First, methyl 6-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 to give the exo olefin-containing compound (E)-methyl 6-(3-methoxybenzylidene)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate, followed by hydrogenation (with 5% Pd/C) according to General Procedure 6, and was purified by chromatography, eluting with heptane-EtOAc, gradient 0 to 40% EtOAc. The material was carried to the next step without further characterization.

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