m-Chloroperbenzoic acid → 5-t-Butoxycarbonyl-2-pyridylmethanol acetate

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Reaction Steps

To a solution of 7.1 g of t-butyl 6-methylnicotinate in 100 ml of dichloromethane, 9.8 g of m-chloroperbenzoic acid is added slowly, and the mixture is stirred at room temperature for 1 hour. The reaction mixture is washed successively with 10% sodium carbonate solution and water, dried over magnesium sulfate, and concentrated. The residue is slowly added to 7.1 g of acetic anhydride at 100°-120° C., and the mixture is refluxed with stirring for 1 hour. After cooling, the remaining acetic anhydride is decomposed with ethanol, and the mixture is concentrated. The residue is neutralized with saturated aqueous potassium bicarbonate and extracted with three 50-ml portions of chloroform. The combined extracts are dried over magnesium sulfate and concentrated to give crude 5-t-butoxycarbonyl-2-pyridylmethanol acetate.

Provenance & Evidence