Methanol → HCID 59180176, compound

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Reaction Steps

The title compound was synthesized from ethyl 6-(biphenyl-4-yl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.1776 g, 0.54 mmol, 1 equiv) and sodium hydroxide (1.36 mL, 13.6 mmol, 10 M, 25 equiv), according to General Procedure 7. A 4-5:1 mixture of methanol (MeOH) and THF (5-6 mL) was used. The resulting product was purified by 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 60% methanol and increasing to 100% over 7 minutes) afforded the title compound (49.3 mg, 30%) with purity by HPLC of 96.6% (UV). LCMS m/e 302.2 (M−H). 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.24-2.37 (m, 1H) 2.66 (ddd, J=8.74, 5.64, 5.53 Hz, 1H) 2.72-2.82 (m, 1H) 2.97 (dd, J=12.96, 4.98 Hz, 1H) 4.31 (dd, J=8.44, 5.37 Hz, 1H) 6.68 (s, 1H) 7.20 (d, J=8.20 Hz, 2H) 7.27-7.34 (m, 1H) 7.40 (t, J=7.63 Hz, 2H) 7.56 (dd, J=15.79, 7.71 Hz, 4H).

Provenance & Evidence