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

2003; Royal Society of Chemistry; Volume: 1; Issue: 7 Linguagem: Inglês

10.1039/b212454h

1477-0539

Diane M. Coe, Rossana Perciaccante, Panayiotis A. Procopiou,

Organic and Inorganic Chemical Reactions

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.