Enantiospecific Synthesis of (R)-3-Amino-4-(2, 4,5-trifluorophenyl)butanoic Acid Using (S)-Serine as a Chiral Pool

Köse A., Gündoʇdu Ö., Aktaş D., Fistikçi M., Altundaş R., SEÇEN H., ...More

Helvetica Chimica Acta, vol.98, no.2, pp.260-266, 2015 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 98 Issue: 2
  • Publication Date: 2015
  • Doi Number: 10.1002/hlca.201400181
  • Journal Name: Helvetica Chimica Acta
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.260-266
  • Hakkari University Affiliated: No

Abstract

Starting from (S)-serine, a new method was developed for the synthesis of the β-amino acid part of sitagliptin in ten steps and with an overall yield of 30%. The crucial step of the synthesis was the ring opening of N- and O-protected (R)-aziridin-2-methanol with (2,4,5-trifluorophenyl)magnesium bromide to give N- and O-protected (R)-2-amino-3-(2,4,5-trifluorophenyl)propan-1-ol.