Methyl iodide → HCID 22914707, compound

Participants

Reaction Steps

To a stirred solution of methyl 2-hydroxy-4-(1-tert-butyloxycarbonyl-3-piperidinyloxy)benzoate from Step 2 above (1.50 g, 4.27 mmol) in DMF (40 mL) under N2 was added NaH (246 mg, 6.41 mmol). The reaction mixture was cooled, then CH3I (0.53 mL, 8.54 mmol) was added via syringe. The reaction mixture was warmed to ambient temperature and stirred for 2 hours. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and aqueous NaHCO3. The ethyl acetate layer was dried (MgSO4), filtered, and evaporated under reduced pressure. The residue was purified using pressurized silica gel column chromatography, eluting with 20% ethyl acetate in hexanes. Methyl 2-methoxy-4-(1-tert-butyloxycarbonyl-3-piperidinyloxy)benzoate was obtained as a colorless oil which crystallized on standing overnight.

Provenance & Evidence