Sulfuric Acid → (S)-2-Hydroxymethyl-azetidine-1-carboxylic acid benzyl ester

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Reaction Steps

Said solution of (S)-azetidine-2-methanol was adjusted to pH 10 by adding 10% sulfuric acid, sodium hydrogen carbonate (0.873 g, 10.5 mmol) was then added and benzyloxycarbonyl chloride (1.75 g, 10.5 mmol) was added at room temperature. Thereafter, stirring was continued for 14 hours. The reaction mixture was adjusted to pH 7 and extracted with ethyl acetate (50 mL×2), the extract was washed with water (50 mL×1), dried over magnesium sulfate and filtered, and the filtrate was concentrated. The concentrate was subjected to column chromatography (Wakogel C-200) using toluene/ethyl acetate as a mobile phase for separation/purification, to give (S)-N-benzyloxycarbonylazetidine-2-methanol as a pale yellow oil (0.495 g, yield 49%). As a byproduct, (S)-2-N-benzyloxycarbonyl-1,4-butanediol was obtained (0.26 g, yield 24%).

Provenance & Evidence