(S,S)-2,8-二氮杂双环[4,3,0]壬烷的合成工艺改进

Process Improvement on the Synthesis of (S,S)-2,8-diazabicyclo[4. 3. 0]nonane

以2,3-吡啶二羧酸为原料,用双(三氯甲基)碳酸酯脱水后与苄胺环合、还原吡啶环制得6-苄基-吡咯并[3,4-b]吡啶-5,7-二酮(5);5用硼烷还原酰亚胺,再经酒石酸拆分及氢解脱苄合成了莫西沙星的关键中间体——(S,S)-2,8-二氮杂双环[4,3,0]壬烷,总收率33%,其结构经1H NMR,13C NMR和MS确证。

6-Benzyl-pyrrolo[ 3,4-b] pyridine-5,7-dione （5） was prepared by the dehydration reaction of 2,3-pyridine carboxylic acid with his （trichloromethyl）carbonate, then cyclization with benzyl- amine, reduction of pyridine ring. The moxifloxacin key intermediate, （ S, S）-2, 8-diazabicyclo [4.3.0 ] nonane, was synthesized by reduction of 5, resolution and debenzylation in overall yield of 33%. The structures were confirmed by 1H NMR, 13C NMR and MS.