Hydrochloric Acid → Ethyl(1RS,5RS,6RS)-6-fluoro-2-oxobicyclo[3.1.0]hexane-6-carboxylate

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Reaction Steps

(2SR)ethyl 2-bromo-2-fluoro-2-[(1RS)-3-oxocyclopentyl]acetate in an amount of 1.00 g was dissolved in 5.0 mL of N,N-dimethylformamide, and 0.84 g of 1,8-diazabicyclo[5.4.0]-7-undecene was added thereto, followed by stirring for 5 hours at room temperature. The reaction mixture was poured into 1M hydrochloric acid, followed by extractions with ethyl acetate twice. The organic layers were combined, and the combined organic layer was subsequently dried over anhydrous sodium sulfate. After the desiccant was filtered off, the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel: Wako gel C200 (produced by Wako Pure Chemical Industries Ltd.), eluent: hexane-ethyl acetate=8:1), thereby yielding 0.68 g of (1RS,5RS,6RS)ethyl 6-fluoro-2-oxobicyclo[3.1.0]hexane-6-carboxylate.

Provenance & Evidence