Methyl iodide → Methyl 3-(((tert-butoxycarbonyl)(methyl)amino)methyl)benzoate

Participants

Reaction Steps

Dissolve 3-(tert-butoxycarbonylamino-methyl)-benzoic acid methyl ester (2.80 g, 10.6 mmol) in dimethylformamide (60 mL). Add 60% sodium hydride dispersion in oil (0.52 g, 13 mmol). Stir for 1 hr. Add methyl iodide (0.81 mL, 13 mmol) and stir for additional 1 hr. Quench the reaction with water and concentrate. Partition the residue between ethyl acetate and water. Separate the organic layer and dry over sodium sulfate. Filter and concentrate. Purify the residue by chromatography (silica gel) eluting with 15-25% ethyl acetate/hexane to provide the title compound (1.70 g, 57%).

Provenance & Evidence