Methyl iodide → methyl 3-(cyclopentyloxy)-4-methoxy-2-(N-methylacetamido)benzoate

Participants

Reaction Steps

A solution of methyl 2-acetamido-3-(cyclopentyloxy)-4-methoxybenzoate (1.6 g, 5.2 mmol, Example 1, Step 4) and anhydrous tetrahydrofuran (30 mL) was added over 5 min to a mixture of sodium hydride (230 mg, 5.75 mmol) and anhydrous tetrahydrofuran (10 mL) at 0° C. under N2. The reaction was allowed to warm to room temperature and after 20 min, cooled back to 0° C. A solution of iodomethane (1.06 g, 0.0075 mol) and anhydrous tetrahydrofuran (10 mL) was added over 3 min. The reaction was allowed to warm to room temperature and after 30 min, concentrated. The residue was diluted with ethyl acetate (40 mL) and washed with brine (10 mL×2). The organic layer was dried, filtered, and concentrated to give methyl 3-(cyclopentyloxy)-4-methoxy -2-(N-methylacetamido)benzoate: MS (ESI): 322.1.

Provenance & Evidence