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In a dry reaction bottle, 128 mL 50% potassium hydroxide solution was added dropwise to a mixture of 15.93 g nitrosomethylurea and 300 mL ethyl ether at −20° C. The resultant solution was added dropwise to a mixture of 11.85 g (R)-1-[2-formyloxy-5-nitro-6-methylaminopyridin-4-yl]piperidine-3-carbamic acid tert-butyl ester (30 mmol) and 240 mL tetrahydrofuran at the same temperature. After addition, the reaction was stopped. Glacial acetic acid was added, and then water and ethyl acetate were added. The reaction solution was extracted with ethyl acetate. The organic phase was combined and washed with saturated brine. The organic layer was dried with anhydrous sodium sulfate, and purified through a column chromatography (Ethyl acetate:Petroleum Ether=1:8). After column chromatography, the solid was recrystallized with ethyl acetate and n-hexane. After the mother liquor was concentrated, 6.6 g yellow solid was obtained, with a yield of 53.8%.

1. additionAfter addition
2. extractionThe reaction solution was extracted with ethyl acetate
3. washwashed with saturated brine
4. dry with materialThe organic layer was dried with anhydrous sodium sulfate
5. custompurified through a column chromatography (Ethyl acetate:Petroleum Ether=1:8)
6. customAfter column chromatography, the solid was recrystallized with ethyl acetate and n-hexane
7. concentrationAfter the mother liquor was concentrated