Tetrahydrofuran → 1-(6-(2-(4-Fluorophenyl)-2-methylpropylamino)pyridin-3-yl)ethane-1,2-diol

Participants

Reaction Steps

N-(2-(4-fluorophenyl)-2-methylpropyl)-5-vinylpyridin-2-amine (158 mg, 0.6 mmol, 1.0 equiv) was added to a foil-covered 20 dram vial and then dissolved in a 50% THF/water mixture (6 mL). Osmium tetraoxide (15 mg, 0.06 mmol, 0.1 equiv) and morpholine N-oxide (103 mg, 0.9 mmol, 1.5 equiv) were added, and the reaction was stirred for 1 h. Additional THF (3 mL) was added, and the reaction was stirred for 3 h. The reaction mixture was then diluted with water (10 mL) and extracted with ethyl acetate (30 mL). The organic layer was dried over Na2SO4, filtered, and concentrated to give a crude solid that was purified by reverse phase column chromatography to give 129 mg (86%) of 1-(6-(2-(4-fluorophenyl)-2-methylpropylamino)pyridin-3-yl)ethane-1,2-diol (m/z [M+H]=305).

Provenance & Evidence