Download PDF
Synthesis 1997; 1997(5): 527-529
DOI: 10.1055/s-1997-1229
short paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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

      >