Development of a scaleable route for the production of cis-N-benzyl-3-methylamino-4-methylpiperidine

被引：32

作者：

Ripin, DHB ^{[1
]}

Abele, S ^{[1
]}

Cai, WL ^{[1
]}

Blumenkopf, T ^{[1
]}

Casavant, JM ^{[1
]}

Doty, JL ^{[1
]}

Flanagan, M ^{[1
]}

Koecher, C ^{[1
]}

Laue, KW ^{[1
]}

McCarthy, K ^{[1
]}

Meltz, C ^{[1
]}

Munchhoff, M ^{[1
]}

Pouwer, K ^{[1
]}

Shah, B ^{[1
]}

Sun, JM ^{[1
]}

Teixeira, J ^{[1
]}

Vries, T ^{[1
]}

Whipple, DA ^{[1
]}

Wilcox, G ^{[1
]}

机构：

[1] Pfizer Inc, Chem Res & Dev, Pfizer Global Res Div, Groton, CT 06340 USA

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2003年 / 7卷 / 01期

关键词：

D O I：

10.1021/op025599x

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

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.

引用

页码：115 / 120

页数：6

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