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Synthesis of 6,6-Dimethyl-3-azabicyclo [3.1.0]hexane via Ru (II)-catalyzed intramolecular cyclopropanation
Medicinal Chemistry Research ( IF 2.6 ) Pub Date : 2023-10-14 , DOI: 10.1007/s00044-023-03158-z Yu Li , Yujie Ma , Shihao Cheng , Chenhu Dong , Xueer Zhong , Jun Xu , Yu Zhao
中文翻译:
Ru(II)催化分子内环丙烷化合成6,6-二甲基-3-氮杂双环[3.1.0]己烷
更新日期:2023-10-15
Medicinal Chemistry Research ( IF 2.6 ) Pub Date : 2023-10-14 , DOI: 10.1007/s00044-023-03158-z Yu Li , Yujie Ma , Shihao Cheng , Chenhu Dong , Xueer Zhong , Jun Xu , Yu Zhao
6,6-Dimethyl-3-azabicyclo[3.1.0]hexane (6,6-DMABH) is a crucial component in several antiviral medications, such as boceprevir and pf-07321332. To enable more efficient synthesis of 6,6-DMABH, we have developed an innovative approach that utilizes intramolecular cyclopropanation of alpha-diazoacetates via Ru (II) catalysis and the Gabriel synthesis. Gram-scale synthesis of 6,6-DMABH from 3-methyl-2-butenol is achieved in seven distinct steps, resulting in a total yield of 28%.
中文翻译:
Ru(II)催化分子内环丙烷化合成6,6-二甲基-3-氮杂双环[3.1.0]己烷
6,6-二甲基-3-氮杂双环[3.1.0]己烷 (6,6-DMABH) 是多种抗病毒药物的重要成分,例如 boceprevir 和 pf-07321332。为了更有效地合成 6,6-DMABH,我们开发了一种创新方法,通过Ru (II) 催化和 Gabriel 合成利用 α-重氮乙酸酯的分子内环丙烷化。由 3-甲基-2-丁烯醇合成 6,6-DMABH 的克级合成通过七个不同的步骤实现,总产率为 28%。