Sodium Hydroxide → HCID 59180157, compound

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Reaction Steps

The title compound was synthesized from methyl 4-p-tolyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.2888 g, 1.2 mmol, 1 equiv) and sodium hydroxide (2.94 mL, 10 M, 25 equiv) according to General Procedure 7. The resulting product was purified by preparative HPLC (water with 0.1% formic acid and 1% acetonitrile/methanol; 50 mm Dynamax HPLC C-18 column; 28 mL/min; 60% to 100% methanol) to give 4-p-tolyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid (37) (76.9 mg, 28%) 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.02-7.10 (m, 4H), 6.50 (s, 1H), 4.13 (t, J=7.20 Hz, 1H), 2.68-2.94 (m, 3H), 2.29 (s, 3H), 2.14-2.25 (m, 1H); LCMS m/e 240 (M−H).

Provenance & Evidence