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Synthesis 2010(2): 255-258  
DOI: 10.1055/s-0029-1217101
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Adrijana Vinter*a, Amir Avdagicb, Vlado Stimaca, Ivana Paleja, Ana Cikosa, Vitomir Sunjicc, Sulejman Alihodzica
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
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Publication History

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

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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