A solution of t-butyl 2-(2-(3-cyano-5-fluorophenyl)-4-formylphenoxy)acetate (21) (120 g, 338 mmol) and MeNH2 (203 mL of a 2M solution in THF, 405 mmol) in methanol (300 mL) was stirred at room temperature for 2 h. Sodium borohydride (12 g, 316 mmol) was added, and the resulting mixture was stirred at room temperature for additional 2 h. Water (30 mL) was added and the MeOH was removed in vacuo. The resulting solution was extracted with EA (3×), and the combined organic layers were dried over Na2SO4, filtered, and concentrated. The crude product t-butyl 2-(2-(3-cyano-5-fluorophenyl)-4-((methylamino)methyl)phenoxy)acetate (22) was used in the next reaction without further purification.
