Process for producing optically active chromene oxide compound
A technology of optical activity and manufacturing method, applied in the fields of titanium organic compounds, organic chemistry methods, organic chemistry, etc., can solve the problem of no reported cases and so on
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Embodiment 1
[0378] (3S, 4S)-6-acetamide-3,4-epoxy-3,4-dihydro-2,2-dimethyl-7-nitro-2H-1-benzopyran (compound (I ))Synthesis
[0379]
[0380] 6-Acetamide-2,2-bis Methyl-7-nitro-2H-1-benzopyran (0.54 g, 2.1 mmol). While stirring the reaction solution, 7.5% aqueous hydrogen peroxide (1.4 g, 3.1 mmol) was added at 28° C. over 10 hours. The addition start time of 7.5% hydrogen peroxide water was taken as the reaction start time, and 7.5% hydrogen peroxide water (0.1g, 0.2mmol) was added at 28°C 14 hours after the reaction started, and then continued stirring at 28°C to calculate from the reaction start time up to 19 hours. After the reaction was completed, dichloromethane (6mL) and distilled water (6mL) were added to the reaction solution, the organic phase was separated, and then the organic phase extracted from the aqueous phase was combined with dichloromethane (6mL), and concentrated by column chromatography. The crude product was purified to obtain compound (I) (0.49 g, yield 86%,...
Embodiment 2
[0384] (3R, 4R)-6-acetamide-3,4-epoxy-3,4-dihydro-2,2-dimethyl-7-nitro-2H-1-benzopyran (compound (II ))Synthesis
[0385]
[0386] 6-Acetamide-2,2- Dimethyl-7-nitro-2H-1-benzopyran (537.4 mg, 2.1 mmol). While stirring the reaction solution, 30% aqueous hydrogen peroxide (302.7 mg, 2.7 mmol) was added at 30°C over 1 second. Stirring was then continued for 7 hours at 30°C. After the reaction, dichloromethane and distilled water were added to the reaction liquid, the organic phase was separated, and the organic phase extracted from the water phase with dichloromethane was combined, and the crude product obtained by concentration was purified by column chromatography. , Obtained yellow powdery compound (II) (0.53 g, yield 93%, optical purity 99.9% ee or higher).
[0387] Analysis conditions: column name CHIRALPAK OJ-RH, eluent acetonitrile / methanol / 0.01M sodium chloride aqueous solution = 1 / 3 / 5 (v / v / v), flow rate 1.5mL / min, column temperature 40°C, retention Time Product o...
Embodiment 3
[0390] Synthesis of (3S,4S)-3,4-epoxy-3,4-dihydro-2,2-dimethyl-6-nitro-2H-1-benzopyran (compound (III))
[0391]
[0392] To a dichloromethane solution (8 mL) of optically active titanium Salalen complex (B) (73 mg, 0.041 mmol) (2.0 mol % relative to the substrate) was added 2,2-dimethyl-6- Nitro-2H-1-benzopyran (0.41 g, 2.0 mmol). While stirring the reaction solution, 30% aqueous hydrogen peroxide (0.24 g, 2.1 mmol) was added at 25° C. over 2 seconds. The start time of addition of 30% hydrogen peroxide water was taken as the reaction start time, and stirring was carried out at 25° C. for 27 hours calculated from the reaction start time. After the reaction finishes, add dichloromethane (6mL) and distilled water (6mL) to the reaction solution, the organic phase is separated, and then the organic phase extracted from the aqueous phase with dichloromethane (6ml) is combined, and the concentrated The crude product was purified by column chromatography to obtain white-yellow p...
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