Synthesis 1989; 1989(8): 622-623
DOI: 10.1055/s-1989-27337
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An Efficient Synthesis of (4S)-(-)-4-Isopropyl-2-oxazolidinone

Peter G. M. Wuts* , Lynn E. Pruitt
  • *Chemical Process Research and Development, The Upjohn Co., 1500-230-4, Kalamazoo, MI 49001, USA
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Publication History

Publication Date:
17 September 2002 (online)

A new, efficient, cost-effective method for the preparation of the Evans' chiral auxiliary (4S)-4-isopropyl-2-oxazolidinone (4) is described. A Schotten-Baumann acylation of valine with phenyl carbonochloridate quantitatively affords the protected valine, which is then reduced with borane in tetrahydrofuran to give an alcohol. Cyclization with a catalytic amount, of potassium tert-butoxide gives 4 in 81% overall yield and in 41-43% after crystallization from ethyl acetate/n-hexane.