Methanol → 4-(3-Fluorobenzyl)-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-fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.075 g, 0.274 mmol) and lithium hydroxide (0.053 g, 1.37 mmol in 3 mL water), according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF (6 mL) was used. The resulting product was purified by column chromatography (Isco CombiFlash) eluting with a gradient of 0-100% EtOAc/heptane to afford the title compound: 30 mg, 42% yield. 1H NMR (400 MHz, METHANOL-d) δ ppm 2.05-2.15 (m, 1H), 2.50-2.60 (m, 1H), 2.60-2.65 (m, 2H), 2.75-2.85 (m, 2H), 3.21-3.28 (m, 1H), 6.30 (s, 1H), 6.85-6.95 (m, 2H), 7.00-7.05 (d, 1H), 7.25-7.35 (q, 1H); 19F NMR δ ppm (m, −116.7); LCMS-MS (ESI−) 258.0 (M−H); HPLC (UV=100%), (ELSD=100%).

Provenance & Evidence