Methyl iodide → [3-(1-Hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-7-yloxy)-propyl]-methyl-carbamic acid tert-butyl ester

Participants

Reaction Steps

NaH (60% dispersion in mineral oil, 0.082 g, 2.05 mmol) was added portionwise to a solution of [3-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-7-yloxy)-propyl]-carbamic acid tert-butyl ester (0.212 g, 0.690 mmol) and MeI (1.03 mL, 2.07 mmol) in anhydrous DMF (5 mL) at 0° C. The reaction was then stirred at rt for 2 h. The mixture was cooled to 0° C., acidified to pH 6 using a sat. NH4Cl, and then extracted with EtOAc. The organic fractions were dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (40% EtOAc/hexane) to give the title compound as a colorless oil: yield 0.17 g (77%).

Provenance & Evidence