Sodium hydride → tert-Butyl 2-(6-(cyanomethoxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Participants

Reaction Steps

To a solution of tert-butyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (500 mg, 1.80 mmol) in DMF (10 mL) was added 60% NaH (215.8 mg, 5.40 mmol) in DMF (5 mL) at 0° C. The reaction mixture was stirred for 30 min, followed by addition of 2-iodoacetonitrile (450.5 mg, 2.70 mmol). The reaction mixture was stirred for an additional 5 h at room temperature, quenched by water (15 mL) at 0° C., and acidified by 1N HCl to pH=7. The resulting mixture was extracted by EtOAc (3×10 mL) and the combined organic layers were dried over anhydrous Na2SO4 and concentrated to dryness. The residue was purified by prep HPLC to give the title compound as a white solid (120 mg, yield: 21%).

Provenance & Evidence