Tetrahydrofuran → 4-(3,5-Dimethylphenyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid

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Reaction Steps

The title compound was synthesized from methyl 4-(3,5-dimethylphenyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (150 mg, 0.45 mmol) and lithium hydroxide monohydrate (108 mg, 4.5 mmol), according to General Procedure 7. A 1:1 mixture of THF and methanol (10 mL) was used. The resulting product was purified by chromatography over silica gel (gradient 0 to 100% EtOAc in heptane over 20 min) to give the title compound. 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.16-2.22 (m, 1H), 2.24 (s, 6H), 2.66-2.92 (m, 3H), 4.08 (t, J=7.35 Hz, 1H), 6.51 (s, 1H), 6.78 (s, 2H), 6.80 (s, 1H). LCMS m/e 256 (M+H) and 95% pure by HPLC.

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