Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate → Methyl 4-(3,5-dimethylbenzyl)-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 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.5 g, 2.79 mmol) was reacted with 3,5-dimethylbenzylmagnesium bromide (28 mL, 6.97 mmol, 0.25 M in THF, 2.5 equiv) according to General Procedure 3 to give (E)-methyl 4-(3,5-dimethylbenzylidene)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate, followed by hydrogenation according to General Procedure 6. The title compound was purified by column chromatography (Isco CombiFlash) eluting with a gradient of 0-100% EtOAc/heptane. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.07-2.18 (m, 1H) 2.33 (s, 6H) 2.50-2.77 (m, 4H) 2.77-2.84 (m, 1H) 3.30 (quin, J=7.08 Hz, 1H) 3.83 (s, 3H) 6.46 (d, J=1.46 Hz, 1H) 6.85 (s, 2H) 6.88 (s, 1H) 9.00 (br. s, 1H).

Provenance & Evidence