Synthesis of 6,6-Dimethyl-3-azabicyclo [3.1.0]hexane via Ru (II)-catalyzed intramolecular cyclopropanation

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-diazoacetat...

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Bibliographic Details
Published in:Medicinal chemistry research 2023-12, Vol.32 (12), p.2501-2504
Main Authors: Li, Yu, Ma, Yujie, Cheng, Shihao, Dong, Chenhu, Zhong, Xueer, Xu, Jun, Zhao, Yu
Format: Article
Language:English
Subjects:
Biochemistry
Biomedical and Life Sciences
Biomedicine
Bioorganic Chemistry
Brief Report
Catalysis
Chemical synthesis
Hexanes
Inorganic Chemistry
Medicinal Chemistry
Pharmacology/Toxicology
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Summary: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%.
ISSN:1054-2523
1554-8120
DOI:10.1007/s00044-023-03158-z