Ethyl 6-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate → HCID 59180228, compound

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Reaction Steps

The title compound was synthesized in two steps. Ethyl 6-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.40 g, 2.23 mmol) was reacted with 3-chloro-5-fluorobenzylmagnesium chloride (0.25 M in diethyl ether, 23.0 mL, 5.6 mmol) according to General Procedure 3 to give the exocyclic olefin-containing compound (Z)-ethyl 6-(3-chloro-5-fluorobenzylidene)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate, followed by hydrogenation according to General Procedure 6 (with Pt2O), and was purified by column chromatography (Isco CombiFlash) eluting with a gradient of 0-20% EtOAc/heptane affording the product as brown solid: 0.055 g (11% yield).

Provenance & Evidence