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Synfacts 2011(1): 0087-0087  
DOI: 10.1055/s-0030-1259112
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Diamine-Free Lithiation of N-Boc Hetero-cycles in THF

Contributor(s): Paul Knochel, Tobias Thaler
G. Barker, P. O’Brien*, K. R. Campos
University of York, UK; Merck Research Laboratories, Rahway, USA
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Publication History

Publication Date:
21 December 2010 (online)

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Significance

A protocol for the diamine-free ­lithiation of N-Boc heterocycles has been reported. Boc-protected pyrrolidines, imidazolidines, and piperazines were efficiently metalated using s-BuLi in THF. Short reaction times between 5-10 minutes were achieved at -30 ˚C.