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Communication | Special issue | Vol 58, No. 1, 2002, pp.119-123
Published online, 1st January, 1970
DOI: 10.3987/COM-02-S(M)54
An Asymmetric Synthesis of 3-Aryl-1,4-oxazin-2-ones: Synthesis of a Key Intermediate of an NK1 Receptor Antagonist

Paul N. Devine,* Bruce S. Foster, Edward J. J. Grabowski, and Paul J. Reider

*Department of Process Reseach, Merck Research Laboratories, Division of Merck & Co., Inc., P. O. Box 200,0, Rahway, New Jersey 07065, U.S.A.


Pyrrolidine derived (S)-lactamide auxiliaries mediate a highly diastereoselective coupling reaction between racemic α-halo acids and N-benzylethanolamine. The adducts are readily cyclized upon treatment with a catalytic amount of TsOH giving the above titled compounds in >90% ee. The 4-fluorophenyl substituted oxazinone thus formed is the key intermediate in the synthesis of a potent NK1 receptor antagonist.