Methanesulfonyl chloride → Tert-butyl 3-(methanesulfonyloxy)azetidine-1-carboxylate

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Reaction Steps

To a solution of tert-butyl 3-hydroxy-1-azetanecarboxylate (4.0 g, 0.023 mol) in anhydrous pyridine (50 mL), methanesulfonyl chloride (5.3 g, 0.046 mol) was added at −20° C. under an atmosphere of nitrogen. The yellow heterogeneous mixture was stirred between −20° C. to −30° C. for one hour, then between 0° C. to −5° C. for two hours. The mixture was poured into ice water (50 mL). The water phase was extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with water (1×50 mL), 5% aquoeus citric acid (4×50 mL), water (1×50 mL), saturated sodium bicarbonate (1×50 mL), and brine (1×50 mL) and dried over sodium sulfate. The solvent was removed under reduced pressure to yield tert-butyl 3-[(methylsulfonyl)oxy]-1-azetanecarboxylate as brownish oil (4.85 g, 0.019 mol).

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