Rapid synthesis of 4-benzyl-4-aminopiperidines by addition of Grignard reagents to N-(1-Boc-piperidin-4-ylidene)-tert-butanesulfinyl imine

被引：9

作者：

Caldwell, John J. ^{[1
]}

Collins, Ian ^{[1
]}

机构：

[1] Inst Canc Res, Canc Res UK Ctr Canc Therapeut, Sutton SM2 5NG, Surrey, England

来源：

SYNLETT | 2006年 / 16期

关键词：

heterocycles; piperidines; imines; Grignard reactions; tandem reactions;

D O I：

10.1055/s-2006-950442

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two concise methods for the synthesis of aryl-substituted 4-benzyl-4-aminopiperidines by the addition of benzyl Grignard reagents to sulfinyl imines were developed. The hydration-prone tert-butanesulfinyl imine derived from N-Boc-piperidin-4-one was trapped as a stable alpha-(N-sulfinyl)aminonitrile, which underwent displacement of the nitrile on treatment with Grignard reagents. Alternatively, benzyl and allyl Grignards added to the sulfinyl imine in situ in a one-pot procedure. Acid deprotection provided various substituted 4-benzyl-4-aminopiperidines.

引用

页码：2565 / 2568

页数：4

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