Sodium hydride → methyl N-(3-chloro-4-fluorophenyl)-N-(3-methoxybenzyl)alaninate

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Reaction Conditions

Reaction Steps

To a flask containing anhydrous DMF (150 mL) was added 1-3 (2.00 g, 8.633 mmol), tertbutylammonium iodide (0.319 g. 0.863 mmol) and 3-methoxy-benzyl bromide (4.340 g, 21.583 mmol) followed by NaH (0.269 g, 11.223 mmol). The resulting solution was heated at 60° C. for 4 days. Upon completion, the reaction mixture was diluted with NaHCO3 (sat. aq), and extracted with ethyl acetate (3×75 mL). The combined organic layers were dried with Na2SO4, filtered, and concentrated. The crude residue was purified by flash column chromatography (SiO2 0-40% ethyl acetate/hexanes gradient) to yield methyl N-(3-chloro-4-fluorophenyl)-N-(3-methoxybenzyl)alaninate (6-1). 1H NMR (300 MHz, CDCl3) δ 7.26 (m, 2H), 6.85 (m, 4H), 6.58 (m, 1H), 4.51 (m, 3H), 3.78 (s, 3H), 3.74 (s, 3H), 1.47 (d, J=7.3 Hz, 3H). MS 352.3 found 352.8 (M+H+) required.

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