An Expeditious Method for the
Preparation of 2-Hydroxy-1,4-dioxane and Its Use in Reductive Alkylation
of Amines

Adrijana Vinter; Amir Avdagic; Vlado Stimac; Ivana Palej; Ana Cikos; Vitomir Sunjic; Sulejman Alihodzic

doi:10.1055/s-0029-1217101

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Synthesis 2010(2): 255-258
DOI: 10.1055/s-0029-1217101

PAPER

An Expeditious Method for the Preparation of 2-Hydroxy-1,4-dioxane and Its Use in Reductive Alkylation of Amines

Adrijana Vinter*^a, Amir Avdagic^b, Vlado Stimac^a, Ivana Palej^a, Ana Cikos^a, Vitomir Sunjic^c, Sulejman Alihodzic^a
^a GlaxoSmithKline Research Centre Zagreb Ltd, Prilaz baruna Filipovica 19, 10000 Zagreb, Croatia
Fax: +385(1)6051001; e-Mail: adrijana.x.vinter@gsk.com;
^b Pliva Croatia Ltd, TAPI R&D, Prilaz baruna Filipovica 19, 10000 Zagreb, Croatia
^c Hegedusiceva 16, 10000 Zagreb, Croatia

Further Information

Publication History

Received 3 September 2009
Publication Date:
06 November 2009 (online)

Abstract
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Abstract

Selective oxidation of diethylene glycol by a ruthenium(VIII) species, obtained in situ from ruthenium(III) chloride-sodium periodate in the presence of a catalytic quantity of water, affords a monoaldehyde in the form of the internal acetal 2-hydroxy-1,4-dioxane. This compound was used in reductive alkylations of selected primary and secondary amines, demonstrating its utility in the preparation of target structures with the 2-(2-hydroxyethoxy)ethylamino unit.

Key words

diethylene glycol - oxidations - reductive alkylations - 2-hydroxy-1,4-dioxane - ruthenium(VIII) catalysis

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