Methyl iodide → 4-[(tert-Butoxycarbonyl-methyl-amino)-methyl]-3-methyl-benzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

Add in portions of 60% sodium hydride dispersion in oil (472 mg, 11.81 mmol) to 4-(tert-butoxycarbonylamino-methyl)-3-methyl-benzoic acid methyl ester (3.0 g, 10.74 mmol) in anhydrous dimethylformamide (50 mL) at 0° C. under argon gas. After complete addition, stir the reaction mixture for 15 min at 0° C. Add methyl iodide (735 μL, 11.8 mmol) to the reaction mixture. Allow the reaction mixture to warm-up to room temperature and stir overnight. Quench the reaction mixture with saturated aqueous ammonium chloride and extract with ethyl acetate (3×). Combine the organic layers, wash with brine, dry over sodium sulfate, and concentrate. Purify the residue by chromatography (silica gel) eluting with 25% ethyl acetate/hexane to give the title compound. MS (m/z): 316 (M+23).

Provenance & Evidence