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Note | Regular issue | Vol 65, No. 1, 2005, pp.149-159
Published online, 12th November, 2004
DOI: 10.3987/COM-04-10220
Stereoselective Gram-Scale Synthesis of (S)-5,5-Dimethyl-4-phenyloxazolidin-2-one

Shigeo Sugiyama,* Satoshi Arai, and Keitaro Ishii*

*Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan


A stereoselective gram-scale synthesis of (S)-5,5-dimethyl-4-phenyloxazolidin-2-one, SuperQuat [(S)-1], is described. The key step is the diastereoselective reduction of (E)-imine (2), which is synthesized from 2-hydroxy-2-methylpropiophenone (4) and (S)-α-methylbenzylamine using sodium borohydride and acetic acid to give (1SS)-2-methyl-1-(α-methyl- benzyl)amino-1-phenylpropan-2-ol (5).