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

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Reaction Steps

The title compound was synthesized in two steps. Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (1.50 g, 8.37 mmol) was reacted with 3-bromobenzylmagnesium bromide (84 mL, 21 mmol) according to General Procedure 3 to give (E)-methyl 4-(3-bromobenzylidene)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate, followed by hydrogenation according to General Procedure 6, and was purified by column chromatography (Isco CombiFlash) eluting with a gradient of 0-30% EtOAc/heptane to afford the title compound: 1.034 g. 1H NMR (400 MHz, ACETONE-d6) δ ppm 2.03-2.11 (m, 1H), 2.47-2.56 (m, 1H), 2.59-2.73 (m, 2H), 2.78 (d, 7.47 Hz, 2H), 3.24-3.32 (m, 1H), 3.72 (s, 3H), 6.32 (d, 1.76 Hz, 1H), 7.20-7.28 (m, 3H), 7.37-7.40 (m, 1H), 7.43 (br s, 1H).

Provenance & Evidence