Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5280586 | Tetrahedron Letters | 2008 | 4 Pages |
Abstract
3,3-Dialkyl-5-(bromomethyl)-1-pyrrolinium bromides, prepared via bromocyclization of N-(2,2-dialkyl-4-pentenylidene)amines by means of bromine in dichloromethane, were reduced to 4,4-dialkyl-2-(bromomethyl)pyrrolidines for the first time using borane dimethyl sulfide in dichloromethane. Furthermore, the latter 2-(bromomethyl)pyrrolidines were transformed into the corresponding piperidin-3-ones through an unprecedented ring expansion-oxidation protocol in dimethylsulfoxide in the presence of potassium carbonate. Reduction of 5,5-dialkylpiperidin-3-ones by means of sodium borohydride in methanol afforded 5,5-dialkyl-3-hydroxypiperidines in good yields.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Matthias D'hooghe, Jan Baele, Jan Contreras, Mark Boelens, Norbert De Kimpe,