An optimized version of Gabriel-type nucleophilic amination

Article abstract of DOI:10.1080/00397910008086868

N-Alkylation of primary alkyl bromides with diethyl N-sodio-N-(t- butoxycarbonyl)phosphoramidate 1 carried out in boiling acetonitrile in the presence of 10mol% of tetrabutylammonium bromide as catalyst leads to the corresponding N-alkyl derivatives 2a-I. Deprotection of 2 by refluxing with p-toluenesulfonic acid in ethanol-affords ammonium tosylates 3a-I in reasonable yields.

Full text of DOI:10.1080/00397910008086868

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Synthetic Communications: An
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An Optimized Version of
Gabriel-Type Nucleophilic
Amination
Andrzej Zwierzak a
a Institute of Organic Chemistry, Technical University
(Politechnika), Zeromskiego 116, PL-90924, Lódź,
Poland
Version of record first published: 04 Dec 2007.
To cite this article: Andrzej Zwierzak (2000): An Optimized Version of Gabriel-Type
Nucleophilic Amination, Synthetic Communications: An International Journal for Rapid
Communication of Synthetic Organic Chemistry, 30:13, 2287-2293
To link to this article: http://dx.doi.org/10.1080/00397910008086868
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