Acetone → 5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-5-[(4-hydroxymethyl-2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane

Participants

Reaction Conditions

Reaction Steps

107 mg (0.20 mmol equivalents) of 5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-5-[(4-formyl-2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane was dissolved in 3.0 mL of ethanol, 10 mg (0.24 mmol equivalents) of sodium borohydride was added thereto, and the mixture was stirred at room temperature (25° C.) for 10 minutes. After completion of the reaction, acetone was added dropwise, and the mixture was concentrated under vacuum. The obtained crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=1/1) to give 101 mg (0.19 mmol equivalents) of 5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-5-{(4-hydroxymethyl-2-nitro-1H-imidazol-1-yl)methyl}-1,3-dioxane.

Provenance & Evidence