Sodium Bicyclo[1.1.1]pentanesulfinate: A Bench-Stable Precursor for Bicyclo[1.1.1]pentylsulfones and Bicyclo- [1.1.1]pentanesulfonamides |
| |
| Authors: | Robin M Bär Dr Patrick J Gross Dr Martin Nieger Prof Dr Stefan Bräse |
| |
| Institution: | 1. Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany;2. Boehringer Ingelheim Pharma GmbH & Co. KG, Birkendorfer Straße 65, 88397 Biberach an der Riß, Germany;3. Department of Chemistry, University of Helsinki, P.O. Box 55 (A. I. Virtasen aukio 1), 00014 Helsinki, Finland |
| |
| Abstract: | Herein, we present the synthesis of the bench-stable sodium bicyclo1.1.1]pentanesulfinate (BCP-SO2Na) and its application in the synthesis of bicyclo1.1.1]pentyl (BCP) sulfones and sulfonamides. The salt can be obtained in a four-step procedure from commercially available precursors in multigram scale without the need for column chromatography or crystallization. Sulfinates are known to be useful precursors in radical and nucleophilic reactions and are widely used in medicinal chemistry. This building block enables access to BCP sulfones and sulfonamides avoiding the volatile 1.1.1]propellane which is favorable for the extension of SAR studies. Further, BCP-SO2Na enables the synthesis of products that were not available with previous methods. A chlorination of BCP-SO2Na and subsequent reaction with a Grignard reagent provides a new route to BCP sulfoxides. Several products were analyzed by single-crystal X-ray diffraction. |
| |
| Keywords: | bicyclo[1 1 1]pentane bioisosteres propellanes sulfonamides sulfur |
|
|
