D. Ripin, Stefan Abele, W. Cai
2003
Citations
0
Influential Citations
34
Citations
Journal
Organic Process Research & Development
Abstract
The synthesis of cis-N-benzyl-3-methylamino-4-methylpiperidine (5) via hydroboration of tetrahydropyridine 3 followed by oxidation and reductive amination was optimized and scaled up to produce 10-kg quantities of product. Three routes to 3 were identified, and the reduction of pyridinium salt 7 was selected as the most preferable to run on-scale. The hydroboration and oxidative workup were carefully studied to optimize throughput on that transformation, as was the reductive amination.