Tetrahedron Letters

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

VS Moshkin, VY Sosnovskikh

Index: Moshkin, Vladimir S.; Sosnovskikh, Vyacheslav Ya. Tetrahedron Letters, 2013 , vol. 54, # 44 p. 5869 - 5872

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Citation Number: 8

Abstract

Abstract 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.

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