Potassium trimethylsilanolate induced cleavage of 1,3-oxazolidin-2- and 5-ones, and application to the synthesis of (R)-salmeterol.

doi:10.1039/B212454H

Paper

Potassium trimethylsilanolate induced cleavage of 1,3-oxazolidin-2- and 5-ones, and application to the synthesis of (R)-salmeterol.

Published Mar 27, 2003 · D. Coe, R. Perciaccante, P. Procopiou

Organic & biomolecular chemistry

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35

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Abstract

A convenient and efficient method for the cleavage of 1,3-oxazolidin-5-ones and 1,3-oxazolidin-2-ones utilising potassium trimethylsilanolate in tetrahydrofuran is described. The benzyloxycarbonyl-protecting group is readily removed under the reaction conditions, whereas the N-benzoyl group is stable. A synthesis of (R)-salmeterol exploiting the 2-oxazolidinone ring as a protecting group for the ethanolamine moiety is also described.

Study Snapshot

Potassium trimethylsilanolate in tetrahydrofuran efficiently cleaves 1,3-oxazolidin-5-ones and 1,3-oxazolidin-2-ones, leading to the synthesis of (R)-salmeterol.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Potassium trimethylsilanolate induced cleavage of 1,3-oxazolidin-2- and 5-ones, and application to the synthesis of (R)-salmeterol.

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References

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Two convenient methods have been developed for hydrolyzing 2-oxazolidinones to vicinal aminoalcohols: using Dowex resin for N-substituted oxazolidinones and polymer supported ethylenediamine for N-unsubstituted oxazo

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Puromycin and 7-deazapuromycin are effective inhibitors of protein biosynthesis and bacterial growth, with high yields and no apparent effect on biological activity when replacing N7 in the purine ring.

Asymmetric synthesis of (−)-pseudoephedrine from (2S,3S)-3-phenyloxiran-2-ylmethanol. Stereospecific interchange of amino and alcohol functions

Asymmetric synthesis of pseudoephedrine from (2S,3S)-3-phenyloxiran-2-ylmethanol with stereospecific amino and alcohol function interchange demonstrates its potential as a pharmaceutical agent.

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This study developed a simple synthesis of chiral alpha-(4-bromobenzyl)alanine ethyl ester, which can be applied to the LFA-1 antagonist BIRT-377, enabling preclinical studies for inflammatory and immune disorders.

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Citations

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