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Park, Cheol-Min
Synthetic & Medicinal Chemistry Lab
Research Interests
  • Organic synthesis, medicinal chemistry, chemical biology

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Concise synthesis of 3,7-dioxa-9-aza-bicyclo[3,3,1]-nonane

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Title
Concise synthesis of 3,7-dioxa-9-aza-bicyclo[3,3,1]-nonane
Author
Park, Cheol-Min
Keywords
TRANSANNULAR CYCLIZATION; AMINE BASICITY
Issue Date
2006-01
Publisher
AMER CHEMICAL SOC
Citation
JOURNAL OF ORGANIC CHEMISTRY, v.71, no.1, pp.413 - 415
Abstract
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.
URI
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DOI
10.1021/jo051982z
ISSN
0022-3263
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PHY_Journal Papers
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