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

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

Organic & biomolecular chemistry (2003-08-21)
Diane M Coe, Rossana Perciaccante, Panayiotis A Procopiou
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Trimethylsilanol, ≥97.5% (GC)
Sigma-Aldrich
Potassium trimethylsilanolate, 90%, technical grade
Sigma-Aldrich
Tris(trimethylsilyl) phosphite, ≥95.0% (GC)
Sigma-Aldrich
Sodium trimethylsilanolate, 95%
Sigma-Aldrich
Lithium trimethylsilanolate, 95%

Social Media

LinkedIn icon
Twitter icon
Facebook Icon
Instagram Icon

MilliporeSigma

Research. Development. Production.

We are a leading supplier to the global Life Science industry with solutions and services for research, biotechnology development and production, and pharmaceutical drug therapy development and production.

© 2021 Merck KGaA, Darmstadt, Germany and/or its affiliates. All Rights Reserved.

Reproduction of any materials from the site is strictly forbidden without permission.