Methanol → HCID 59180185, compound

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Reaction Steps

The title compound was synthesized from methyl 4-(4-bromobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.0998 g, 0.3 mmol, 1 equiv) and lithium hydroxide (0.8 mL, 2 M aqueous, 1.6 mmol, 5.3 equiv), according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF (5 mL) was used. The resulting product was purified via preparative HPLC using the Chromeleon purification system. A 0.1% formic acid/1% acetonitrile mixture in water (aqueous phase) and methanol (no modifier added—organic phase) using a 50 mm Dynamax HPLC C-18 column at 28 mL/min (initial gradient of 70% methanol and increasing to 100% over 7 minutes) afforded the title compound. 67.2 mg, with purity by HPLC of 100% (UV). LCMS m/e 318 (M−H). 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.02-2.16 (m, 1H), 2.49-2.67 (m, 3H), 2.74 (dd, J=9.77, 7.37 Hz, 2H), 3.19-3.29 (m, 1H), 6.29 (s, 1H), 7.11 (d, J=8.35 Hz, 2H), 7.41 (q, J=4.25 Hz, 2H).

Provenance & Evidence