Title
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Synthesis of 2-(3-hydroxy-2-methyl-1-alkenyl)-1-pyrrolines and 2-(3-hydroxybutyl)-1-pyrroline using alpha-lithiated 2-methyl-1-pyrroline
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Author
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Abstract
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Condensation of 2-methyl-1-pyrroline with chloroacetone or 3-chloro-2-butanone using LDA in THF afforded novel 2-(3-hydroxy-2-methyl-1-alkenyl)-1-pyrrolines via a peculiar reaction mechanism instead of the anticipated 2-(3-oxobutyl)-1-pyrrolines. The intermediacy of 2-(2,3-epoxy-2-methylalkyl)-1-pyrrolines in the latter transformation was demonstrated by immediate reductive epoxide ring opening utilizing lithium aluminium hydride in diethyl ether. Furthermore, 2-(3-oxobutyl)-1-pyrroline was prepared via an alternative approach through alkylation of 2-methyl-1-pyrroline with 3-chloro-2-(methoxymethyloxy)-1-propene using LDA in THF, followed by acid hydrolysis. Reduction of 2-(3-oxo butyl)-1-pyrroline by sodium borohydride in methanol afforded the corresponding 2-(3-hydroxybutyl)-1-pyrroline in good yield. (C) 2009 Elsevier Ltd. All rights reserved. |
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Language
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English
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Source (journal)
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Tetrahedron. - Oxford, 1957, currens
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Publication
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Oxford
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2009
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ISSN
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0040-4020
[print]
1464-5416
[online]
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DOI
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10.1016/J.TET.2009.02.050
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Volume/pages
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65
:18
(2009)
, p. 3753-3756
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ISI
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000265264400028
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Full text (Publisher's DOI)
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Full text (publisher's version - intranet only)
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