Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate → HCID 59180160, compound

Participants

Reaction Steps

The title compound was synthesized in two steps. First, methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (200 mg, 1.12 mmol) was reacted with (biphenyl-4-ylmethyl)magnesium bromide (0.25 M in diethyl ether, 17.9 mL, 4.46 mmol) according to General Procedure 3. The resulting crude product was converted to the title compound by hydrogenation according to General Procedure 6 (with 10% Pd/C). The crude product was purified by column chromatography (Isco CombiFlash) eluting with a gradient of 0-40% EtOAc/heptane to afford the title compound, 122 mg. 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.08-2.19 (m, 1H), 2.51-2.72 (m, 3H), 2.75-2.87 (m, 2H), 3.26-3.35 (m, 1H), 3.76 (s, 3H), 6.34 (s, 1H), 7.24-7.28 (m, 2H), 7.28-7.33 (m, 1H), 7.38-7.44 (m, 2H), 7.51-7.56 (m, 2H), 7.59-7.63 (m, 2H); LCMS-MS (ESI+) 354.0 (M+Na).

Provenance & Evidence