Water → (2S)-1-((tert-butoxy)carbonyl)azetidine-2-carboxylic acid

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Reaction Steps

(S)-(−)-2-Azetidinecarboxylic acid (Aldrich Chemical Company, Milwaukee, Wis.) (1.00 g, 9.89 mmol) is dissolved in 12 mL of 1:1 dioxane:water. Triethylamine (2.1 mL, 14.84 mmol) is added followed by BOC-ON (2.68 g, 10.9 mmol). The mixture is stirred for 6.75 hours then poured onto water (50 mL) and extracted with ether (7 times, 50 mL each). The aqueous solution is cooled in an ice-bath and the pH adjusted to approximately 2.5 with ice-cold 1N HCl solution. The resulting solution is extracted with methylene chloride (3 times, 50 mL each). The combined organic extracts are dried over MgSO4, filtered and concentrated in vacuo to afford an oil. Hexane (100 mL) is added to this oil and the mixture placed in the freezer overnight. The hexane is decanted and the product (1) dried under vacuum to afford a white solid. ISMS: MH+ 202.2

Provenance & Evidence