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Synthesis 1990; 1990(11): 1011-1012
DOI: 10.1055/s-1990-27079
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Synthesis and N-Alkylation of 5-Bromomethyl-5-methyl-1,4,7,10-tetraoxa-13-azacyclopentadecane

Ryuhei Wakita* , Misao Tsubakihara, Yohji Nakatsuji, Mitsuo Okahara
  • *Department of Applied Chemistry, Faculty of Engineering, Osaka University, Yamadaoka, Suita, Osaka, Japan
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Publication Date:
17 September 2002 (online)

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5-Bromomethyl-5-methyl-1,4,7,10-tetraoxa-13-azacyclopentadecane (monoaza-15-crown-5) was prepared by the reaction of 4-bromomethyl-4-methyl-1,8-ditosyloxy-3,6-dioxaoctane, prepared from the corresponding dihydroxy compound, by reaction with bis-(2-hydroxyethyl)amine under basic conditions in 37% yield, without protection of the reactive bromomethyl and amino groups. The product, monoaza-15-crown-5, can be N-alkylated in 42-70% with alkyl halide/sodium carbonate in dioxane.