Chemical Synthesis of the ODM-201’s Diastereomers through an Efficient Intramolecular 1,3-Dipolar Cycloaddition

Tingting Pan; Chunguang Xia; Huijuan Jiang; Zhongtang Zhang; Xueyan Zhu; Yulei Yang

doi:10.1248/cpb.c17-00176

Regular Articles

Chemical Synthesis of the ODM-201’s Diastereomers through an Efficient Intramolecular 1,3-Dipolar Cycloaddition

Tingting Pan, Chunguang Xia, Huijuan Jiang, Zhongtang Zhang, Xueyan Zhu, Yulei Yang

Author information

Keywords: ODM-201, diastereomer, synthesis, intramolecular 1,3-dipolar cycloaddition

JOURNAL FREE ACCESS FULL-TEXT HTML
Supplementary material

2017 Volume 65 Issue 6 Pages 582-585

DOI https://doi.org/10.1248/cpb.c17-00176

Browse “Advance online publication” version

Details

Abstract

An efficient synthesis of ODM-201’s diastereomers has been developed from (R)-methyl 3-hydroxybutanoate or (S)-methyl 3-hydroxybutanoate, respectively, with high overall yield and excellent diastereomeric purity. The key step in this synthesis is the preparation of the key intermediate (R)-5-(1-((tert-butyldimethylsilyl)oxy)ethyl)-1H-pyrazole-3-carboxylic acid or (S)-5-(1-((tert-butyldimethylsilyl)oxy)ethyl)-1H-pyrazole-3-carboxylic acid through intramolecular 1,3-dipolar cycloaddition of the vinyl diazo carbonyl compounds.

Graphical Abstract Fullsize Image

Corresponding author

Register with J-STAGE for free!