A simple two-step synthesis of 2-(alkylamino)-1-arylethanols, including racemic adrenaline, from aromatic aldehydes via 5-aryloxazolidines

TETRAHEDRON LETTERS

卷:54

Article

Moshkin, Vladimir S.¹  Sosnovskikh, Vyacheslav Ya.¹ 

[1] Ural Fed Univ, Dept Chem, Ekaterinburg 620000, Russia

关键词: Benzaldehydes;    Nonstabilized azomethine ylides;    [3+2] Cycloaddition;    5-Aryloxazolidines;    Phenethylamines;    Epinephrine (adrenaline);   

DOI  :  10.1016/j.tetlet.2013.08.083

来源: Elsevier

【 摘 要 】

Benzaldehydes react smoothly with nonstabilized azomethine ylides, generated in situ from sarcosine/ formaldehyde or N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine, to give 5-aryloxazolidines as intermediates. These were converted into 2-(alkylamino)-1-arylethanols in good yields by simple heating in methanol with hydrochloric acid, or by treatment with hydrazine hydrate in ethanol. (C) 2013 Elsevier Ltd. All rights reserved.

【 授权许可】

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