Twisted amide reduction under Wolff-Kishner conditions: Synthesis of a benzo-1-aza-adamantane derivative

被引：54

作者：

Bashore, CG ^{[1
]}

Samardjiev, IJ ^{[1
]}

Bordner, J ^{[1
]}

Coe, JW ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 11期

关键词：

D O I：

10.1021/ja028152c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A synthesis of 4,5-benzo-1-aza-tricyclo[4.3.1.1(3,8)]undecane (1), a benzo-1-aza-adamantane derivative, is described and features a previously unknown application of the Wolff-Kishner reduction of a nonresonance stabilized or "twisted" amide. An intermediate amino ester is converted to a severely "twisted amide", which, when exposed to hydrazine in alcohol, provides the corresponding "twisted" amino hydrazone. Wolff-Kishner conditions (KOH/ethylene glycol, 200 degreesC) provide the reduced target 1 without hydrolysis to amino acid derivatives. These operations are conveniently performed in a single flask in high yield.

引用

页码：3268 / 3272

页数：5

共 45 条

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