Concise synthesis of 3,7-dioxa-9-aza-bicyclo[3,3,1]-nonane
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- Concise synthesis of 3,7-dioxa-9-aza-bicyclo[3,3,1]-nonane
- Park, Cheol-Min
- TRANSANNULAR CYCLIZATION; AMINE BASICITY
- Issue Date
- AMER CHEMICAL SOC
- JOURNAL OF ORGANIC CHEMISTRY, v.71, no.1, pp.413 - 415
- The basicity of an amine has a great impact on physicochemical properties and pharmacokinetics. To attenuate the basicity of morpholine, a bicyclic amine was designed and synthesized with the introduction of an additional β-oxygen. A transannular cyclization and reduction of a bridgehead α-chloro amine functionality produces the topographically unusual amine (pKa = 6.7) in good yield.
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