Dimethyl Sulfide → HCID 59370752, compound

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Reaction Conditions

Reaction Steps

Under nitrogen atmosphere, 2-chloro-1-(4-fluoro-3-nitrophenyl)ethanone (5.4667 g) which can be prepared according to the method described in Reference example 64, etc. was dissolved in dehydrated THF (100 mL), added with 1 mol/L-(R)—CBS-toluene solution (7.5 mL; manufactured by Sigma-Aldrich Co.), followed by cooling to 0° C. To the resulting solution, BH32.SMe2 (10 mL; manufactured by Sigma-Aldrich Co.) was added dropwise over 10 minutes and the mixture was stirred at 0° C. for 2 hours. An aqueous solution of ammonium chloride was added to the reaction solution and extraction was carried out twice with ethyl acetate. The organic layer was washed once with brine, dried over magnesium sulfate, and then the solvent was evaporated under reduced pressure. The resulting residue was added with 2-propanol (100 mL) and an aqueous solution of 1 mol/L-sodium hydroxide (25 mL; manufactured by Kanto Chemical Co., Inc.), and the mixture was stirred at 0° C. for 10 minutes. The reaction solution was poured to water and extracted twice with ethyl acetate. The organic layer was washed once with brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography (“COLUMN-8”; n-hexane:ethyl acetate=88:12→67:33) to obtain the title compound (4.2885 g, optical purity; 92% ee).

Provenance & Evidence