Elsevier

Tetrahedron: Asymmetry

Volume 3, Issue 4, April 1992, Pages 539-554
Tetrahedron: Asymmetry

S-[1-(2,3-diaminophenoxy)]-3′-(N-t-butylamino)propan-2′-ol-simplified asymmetric synthesis with CD and chiral HPLC analysis

https://doi.org/10.1016/S0957-4166(00)80261-XGet rights and content

Abstract

S-[1-(2,3-Diaminophenoxy)]-3′-(N-t-butylamino)propan-2′-ol is important as a precursor in the radiosynthesis of a 11C-labelled radioligand (S-[carbonyl-11C]CGf 12177) for the study of β-receptors in living man. The asymmetric synthesis of this precursor has been simplified based on the reaction of readily available 2-amino-3-nitrophenol and the chiral auxiliary, S-glycidyl-3-nitrobenzenesulphonate, followed by treatment of the resultant S-epoxide with t-butylamine and reduction with hydrogen in the presence of palladium on carbon. Chiral HPLC methods have been successfully developed to monitor the enantiomeric purity of the chiral auxiliary and of all intermediates in the asymmetric synthesis. All intermediates and products have been studied by CD. It has been demonstrated by chiral HPLC that S-CGP 12177 can be prepared in > 98.4% e.e. from the synthesised S-precursor. R-CGP 12177 (e.e.>96.2%) was prepared analogously.

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