Application | fluoroquinolones are mainly used for the treatment of respiratory infections, urinary tract infections, sexually transmitted diseases, skin and Skin soft tissue infections. (1 α,5 α,6 α)-6-amino-3-azabicyclo [3.1.0] hexane-3-carboxylic acid 1, 1-dimethylethyl Ester is an intermediate for the preparation of histone deacetylase (HDAC) inhibitors with Class I selectivity and good oral bioavailability. It can be used in the synthesis of alatoxacin mesylate. |
preparation | preparation of REL-(1R,5S,6S)-6-amino-3-azabicyclo [3.1.0] hexane-3-carboxylic acid tert-butyl ester. Take three dry reaction bottles, one with a calcium chloride dryer, one with a dropping funnel, tetrahydrofuran solution to be anhydrous treatment in advance. Weigh tert-butyl formyl chloride and dissolve in 180mL anhydrous tetrahydrofuran solution, start stirring device. After dissolution, the solution was slowly added to 200ml of tetrahydrofuran solution (3-azabicyclo [3.1.0] hexane-6-amine was dissolved in tetrahydrofuran solution) in ice-water bath condition, solid was precipitated immediately, and stirring was continued at 35 ° C. For 4 hours after addition. The reaction progress was checked by thin layer chromatography. After completion of the reaction, the reaction solution was cooled, 400ml of ice water was added to the reaction to complete precipitation of the product, and a pale yellow solid was obtained by Suction filtration. After drying, it was crystallized from absolute ethanol to obtain tert-butyl REL-(1R,5S,6S)-6-amino-3-azabicyclo [3.1.0] hexane-3-carboxylate. |