Crystallization-induced Diastereomeric Transformation of Chiral Ozanimod Key Intermediate using Homogeneous Ir-based Racemization Catalyst

02 May 2024, Version 2
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Crystallization-induced diastereomeric transformation of a solid solution salt composed of a chiral primary amine, 4-cyano-1-aminoindane, and di-p-toluoyl-L-tartaric acid was achieved using (pentamethylcyclopentadienyl)iridium(III) diiodide dimer as a racemization catalyst. The enrichment continued until the composition of the solid phase was in equilibrium with the liquid phase at 0% diastereomeric excess.

Keywords

deracemization
resolution
chirality
diastereomeric salt
solid solution

Supplementary materials

Title
Description
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Supporting Information
Description
General, Synthesis of (pentamethylcyclopentadienyl)iridium(III) diiode dimer, Crystal structures of salts composed of 1 and various acid compounds, Screening of racemization conditions for 1 or salt 1·2 , Deracemization of salt 1·2 in THF, Chiral HPLC analysis, and Construction of ternary phase diagram
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