Sodium hydride → (trans)-N-[[2-(3-methoxyphenyl)cyclopropyl]methyl]butanamide

Participants

Reaction Steps

(trans)-N-Methoxy-N-methyl-2-(3-methoxyphenyl) cyclopropanecarboxamide: To a suspension of NaH (16.27 g, 0.68 mol) in DMSO (375 mL) was added solid trimethylsulfoxonium iodide (149.16 g, 0.68 mol) in small portions. After the foaming had subsided (40 min), a solution of (trans)-N-methoxy-N-methyl-3-(3-methoxyphenyl)-2-propenamide (50 g, 0.23 mol) in DMSO (50 mL) was added dropwise, maintaining the temperature between 35°-40° C. Stirring was continued for 18 h at room temperature, followed by the dropwise addition of saturated NH4Cl (400 mL) and extraction with ethyl acetate. The organics were combined, washed with brine, dried (K2CO3), and concentrated to give a red oil which was then purified by Kugelrohr distillation (130° C., 0.5 mm Hg) to afford the title compound as a white wax (52.47 g, 100%): 1H NMR (300 MHz, CDCl3) δ 0.82-0.88 (m, 1H), 1.20-1.30 (m, 1H), 1.59-1.62 (m, 1H), 2.40-2.45 (m, 1H), 3.22 (s, 3H), 3.68 (s, 3H), 3.79 (s, 3H), 6.61-6.72 (m, 3H), 7.18 (t, J=6.0 Hz, 1H).

Provenance & Evidence