Toluene → (e)-Tert-butyl 3-(trans-1-benzyl-4-(3-methoxyphenyl)pyrrolidin-3-yl)acrylate

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A mixture of Example 261C (1.86 g, 6.3 mmol) and t-butoxylcarbonylmethylenetriphenylphosphorane (2.37 g, 6.3 mmol) in toluene (15 mL) was heated at 110° C. for 1 hour. The volatiles were removed and the crude material was purified by silica gel column chromatography eluting with hexanes and ethyl acetate (3:1) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.32 (m, 4H), 7.25 (m, 1H), 7.18 (d, J=8.4 Hz, 1H), 6.85 (m, 2H), 6.76 (d, J=15.3 Hz, 1H), 5.69-5.61 (m, 1H), 3.73 (s, 3H), 3.70 (d, J=15.0 Hz, 1H), 3.59 (d, J=15.0 Hz, 1H), 3.13 (m, 1H), 2.98 (m, 3H), 2.62 (m, 1H), 2.53 (m, 1H), 1.39 (s, 9H).

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