Development of a Scaleable Route for the Production of cis-N-Benzyl-3-methylamino-4-methylpiperidine

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• 作者：David H. Brown Ripin ; Stefan Abele ; Weiling Cai ; Todd Blumenkopf ; Jeffrey M. Casavant ; Jonathan L. Doty ; Mark Flanagan ; Christian Koecher ; Klaus W. Laue ; Keith McCarthy ; Cliff Meltz ; Mike Munchhoff ; K
• 刊名：Organic Process Research & Development
• 出版年：2003
• 出版时间：January 2003
• 年：2003
• 卷：7
• 期：1
• 页码：115 - 120
• 全文大小：78K
• 年卷期：v.7,no.1(January 2003)
• ISSN：1520-586X

文摘

The synthesis of cis-N-benzyl-3-methylamino-4-methylpiperidine(5) via hydroboration of tetrahydropyridine 3 followed byoxidation and reductive amination was optimized and scaledup to produce 10-kg quantities of product. Three routes to 3were identified, and the reduction of pyridinium salt 7 wasselected as the most preferable to run on-scale. The hydroboration and oxidative workup were carefully studied to optimizethroughput on that transformation, as was the reductiveamination.