Potassium trimethylsilanolate induced cleavage of 1,3-oxazolidin-2- and 5-ones, and application to the synthesis of (R)-salmeterol.
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.
Coe
Diane M
DM
GlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire, UK SG1 2NY.
Perciaccante
Rossana
R
Procopiou
Panayiotis A
PA
D000318:Adrenergic beta-Agonists / Q000138:chemical synthesis*; D000420:Albuterol / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D015394:Molecular Structure; D023303:Oxazolidinones / Q000737:chemistry*; D000068299:Salmeterol Xinafoate; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D000318:Adrenergic beta-Agonists; D023303:Oxazolidinones; D014297:Trimethylsilyl Compounds; D000068299:Salmeterol Xinafoate; D000420:Albuterol; C055926:trimethylsilanol