NDLI: Rapid Synthesis of 4-Benzyl-4-aminopiperidines by Addition of Grignard Reagents to N-(1-Boc-Piperidin-4-ylidene)-tert-butanesulfinyl Imine

Content Provider	Scilit
Author	Collins, Ian Caldwell, John
Copyright Year	2006
Description	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 α-(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.
Related Links	http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2006-950442.pdf
Ending Page	2568
Page Count	4
Starting Page	2565
ISSN	09365214
e-ISSN	14372096
DOI	10.1055/s-2006-950442
Journal	Synlett
Issue Number	16
Volume Number	2006
Language	English
Publisher	Georg Thieme Verlag KG
Publisher Date	2006-09-22
Access Restriction	Open
Subject Keyword	Organic Chemistry Grignard Reactions
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry

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