Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate → Methyl 4-(3-fluorobenzyl)-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 (0.50 g, 2.79 mmol) was reacted with 3-fluorobenzylmagnesium chloride (0.25 M in diethyl ether, 52 mL, 13 mmol) according to General Procedure 3. The resulting exo-olefin ((E)-methyl 4-(3-fluorobenzylidene)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate) was then converted to the title compound by hydrogenation according to General Procedure 6. In this example, Degussa type, 5% palladium on carbon (0.100 g, 0.1 mmol) was used, and the reaction placed under a hydrogen atmosphere in a Parr shaker (40 PSI) for 2 hours. Purification by column chromatography (Isco CombiFlash) eluting with a gradient of 0-40% EtOAc/heptane afforded the title compound. 0.075 g. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.03-2.11 (m, 1H), 2.47-2.56 (m, 1H), 2.59-2.73 (m, 2H), 2.78 (d, J=7.4 Hz, 2H), 3.24-3.32 (m, 1H), 3.81 (s, 3H), 6.39 (d, J=1.7 Hz, 1H), 6.90-7.00 (m, 3H), 7.20-7.35 (m, 1H), 8.94 (br s, 1H).

Provenance & Evidence