2-Nitroimidazole → 5-(t-butyldimethylsiloxymethyl)-2,2-dimethyl-5-[(2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane

Participants

Reaction Conditions

Reaction Steps

578 mg (1.64 mmol equivalents) of 5-bromomethyl-5-(t-butyldimethylsiloxymethyl)-2,2-dimethyl-1,3-dioxane was dissolved in 10 mL of dimethylformamide, 186 mg (1.64 mmol equivalents) of 2-nitroimidazole and 680 mg (4.92 mmol equivalents) of potassium carbonate were added thereto, and the mixture was heated to 100° C. for 18 hours. After completion of the reaction, the reaction liquid was cooled to room temperature (25° C.), a saturated aqueous solution of ammonium chloride and water were added thereto, and the mixture was extracted three times with ethyl acetate. The combined ethyl acetate layers were washed with water and brine, then dried with anhydrous magnesium sulfate and subsequently concentrated under vacuum, and the obtained crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=3/1) to give 363 mg (0.942 mmol equivalents) of 5-(t-butyldimethylsiloxymethyl)-2,2-dimethyl-5-[(2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane.

Provenance & Evidence