Organic & Biomolecular Chemistry 2003-04-07

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

Diane M Coe, Rossana Perciaccante, Panayiotis A Procopiou

Index: Org. Biomol. Chem. 1(7) , 1106-11, (2003)

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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.

Related Compounds

  • Tris(trimethylsily...

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