Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate → Methyl 4-(3-chlorobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

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Reaction Steps

The title compound was synthesized in two steps. First, methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (447 mg, 2.5 mmol) was reacted with 3-chlorobenzylmagnesium chloride (0.25 M in hexanes, 25 mL, 6.3 mmol) according to General Procedure 3. The resulting products were then converted to the title compound by hydrogenation according to General Procedure 6 (with Pt2O). The crude product was purified by column chromatography eluting with heptane-EtOAc, gradient 0 to 40% EtOAc to afford the title compound. 262 mg. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.04-2.15 (m, J=12.57, 8.03, 6.17, 6.17 Hz, 1H) 2.52-2.64 (m, 1H) 2.64-2.72 (m, 2H) 2.74-2.83 (m, 2H) 3.81 (s, 3H) 6.39 (d, J=1.37 Hz, 1H) 7.07 (d, J=8.25 Hz, 1H) 7.21 (d, J=1.81 Hz, 2H) 7.22-7.26 (m, 1H) 7.28-7.32 (m, 1H) 8.75 (br. s, 1H).

Provenance & Evidence