Methanol → 4-((4'-(Hydroxymethyl)biphenyl-3-yl)methyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid

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Reaction Steps

The title compound was synthesized from methyl 4-((4′-(hydroxymethyl)biphenyl-3-yl)methyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.012 g, 0.033 mmol) and lithium hydroxide (0.016 g, 0.38 mmol in 0.5 mL water), according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF (1 mL) was used. The resulting product was purified by reverse phase HPLC, eluting with a gradient of 40-100% MeOH: water (with 0.1% formic acid) to afford the title compound: 4.5 mg, 39% yield. 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.10-2.18 (m, 1H), 2.52-2.63 (m, 3H), 2.79-2.91 (m, 2H), 3.33 (d, J=1.61 Hz, 1H), 4.64 (s, 2H), 6.39 (s, 1H), 7.19 (s, 1H), 7.34 (s, 2H), 7.42 (s, 3H), 7.56 (d, J=8.30 Hz, 2H); LCMS-MS (ESI−) 346.2 (M−H); HPLC (UV=93.1%), (ELSD=100%).

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