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Synthesis 1997; 1997(5): 527-529
DOI: 10.1055/s-1997-1229
short paper
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Synthesis of N-(tert-Butoxycarbonyl)-N,O-isopropylidene Serinal from Serine Methyl Ester by a Reduction-Oxidation Sequence

Alessandro Dondini* , Daniela Perrone
  • *Dipartimento di Chimica, Laboratorio di Chimica Organica, Università, I-44100 Ferrara, Italy, Fax +39(532)240709; E-Mail ADN@DNS.UNIFE.IT
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Publication History

Publication Date:
31 December 2000 (online)

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The title aldehyde is prepared by LiAlH4 reduction of the corresponding serine derived methyl ester to the alcohol and Swern oxidation of the latter. The aldehyde is obtained in 94% yield and 96-98% enantiomeric purity. This method avoids some problems encountered in the synthesis of the same aldehyde by direct controlled DIBAL reduction of the ester.

serine methyl ester - N-Boc-serinol - N-Boc-serinal - Swern oxidation