Water → cis-3-(4-Chlorophenyl)-3a,4,6,6a-tetrahydro-pyrrolo[3,4-d]isoxazole-5-carboxylic acid tert-butyl ester

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Reaction Steps

To N-Boc pyrroline (480 mg; 2.83 mmol) and chloro oxime 2a (557 mg; 2.93 mmol) in ethyl acetate (15 mL), was added dropwise triethylamine (0.4 mL) in ethyl acetate (15 mL). The reaction mixture was stirred at room temperature for 24 hours. An additional portion of chloro oxime 2a (234 mg; 1.23 mmol) and triethylamine were added. After stirring overnight, the reaction mixture was poured into water (50 mL) and extracted. The organic layer was dried (MgSO4), filtered and evaporated. Chromatography with 30% ethyl acetate/hexanes yielded 3a as a white solid.

Provenance & Evidence