Methyl iodide → HCID 66646915, compound

Participants

Reaction Steps

The product from Example 22C (620 mg, 1.47 mmol) in DMF (5 mL) was treated with NaH (60%)(88 mg, 2.2 mmol). The mixture was stirred for 10 min at rt. To the mixture was added dropwise iodomethane (251 mg, 1.57 mmol). The reaction was stirred at rt for 12 hrs. The reaction mixture was quenched with water and extracted with EtOAc. The organic was dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-100% ethyl acetate in hexanes) to afford 574 mg (90%) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 1.91-2.02 (m, 2H) 3.09 (dd, J=9.82, 5.52 Hz, 1H) 3.15 (dd, J=9.82, 4.91 Hz, 1H) 3.31 (s, 3H) 3.78 (s, 6H) 3.81-3.93 (m, 2H) 3.94-4.06 (m, 2H) 6.77-6.87 (m, 4H) 7.16-7.23 (m, 1H) 7.26-7.37 (m, 6H) 7.40-7.48 (m, 2H).

Provenance & Evidence