Water → tert-Butyl 4-{[6-(1,2-dihydroxyethyl)-2-(trifluoromethyl)pyrimidin-4-yl]oxy}piperidine-1-carboxylate

Participants

Reaction Steps

To a solution of tert-butyl 4-{[2-(trifluoromethyl)-6-vinylpyrimidin-4-yl]oxy}piperidine-1-carboxylate (614 mg, 1.64 mmol) in methanol (7 mL) and tert-butyl alcohol (5.2 mL) was added TV-methylmorpholine TV-oxide (212 mg, 1.81 mmol) and water (5.2 mL). To this solution was then added osmium tetraoxide (20.9 mg, 0.0822 mmol). After stirring for 3 hours, another equivalent of TV-methylmorpholine TV-oxide was added. The reaction was stirred at room temperature overnight. The solution was concentrated and diluted with water and extracted with ethyl acetate twice, washed with brine, dried over Na2SO4, filtered and concentrated. The crude was purified by flash chromatography on a silica gel column to give the desired product. LCMS (M+H)+: 408.2.

Provenance & Evidence