Synthesis of 1-tert-butyl-4-chloropiperidine: Generation of an N-tert-butyl group by the reaction of a dimethyliminium salt with methylmagnesium chloride
(Chemical Equation Presented) Two efficient routes to 1-tert-butyl-4- chloropiperidine are described. In the first route, the key thionyl chloride mediated chlorination reaction features the use of tetrabutyl-ammonium chloride as an additive that effectively suppresses the formation of an elimination-derived side product. In the second route, a novel alternative synthesis of 1-tert-butyl-4-chloropiperidine was developed in which the tertiary butyl group on the nitrogen is efficiently generated through the addition of methylmagnesium chloride to a dimethyliminium salt in 71% overall yield.
Amato, Joseph S.,Chung, John Y. L.,Cvetovich, Raymond J.,Gong, Xiaoyi,McLaughlin, Mark,Reamer, Robert A.
p. 1930 - 1933
(2007/10/03)
Sulfamylbenzoic acids
Certain mono- and disubstituted-5-sulfamylbenzoic acids, many of which are novel, and their use in lowering blood lipid levels in mammals.
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(2008/06/13)
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