6´-Aminocinchonidine Base – Fine Chemical

Introduction

6´-Aminocinchonidine Base (CAS-No. 2143936-34-7) belongs to a new class of Cinchona alkaloids, bearing a free amio group in the C6’-position. Despite its position far away from the stereocenters, the amino group proves crucial to obtain high enantioselectivity in synthetically relevant reactions like Michael additions etc..
On the other hand the free C6’ amino group can be further functionalized to improve catalytic performance. A wide range of completely new chiral ligands and catalysts are easily accessible.

Please also take a look into our free of charge Chiral Catalyst Search Database, containing several examples.

Physical properties

6´-Aminocinchonidine Base (CAS-No. 2143936-34-7) is a white or almost white, crystalline powder or it consists of fine, colourless needles, being soluble in methanol. The melting point is in the range of 252 – 255 °C. This compound is not hygroscopic and contains less than 5.0 % water. 6`-Amonocinchonidine could be stored at ambient conditions in well-closed, light-resistant containers.

Synonyms

6`-Aminocinchonidine, (8S,9R)-6`-Aminocinchonan-9-ol, (8α,9R)-6`-Aminocinchonan-9-ol and (R)-[(2S,4S,5R)-5-Ethenyl-1-azabicyclo[2.2.2]oct-2-yl](6-aminoquinolin-4-yl)methanol.

NMR-data

The following spectroscopic techniques were used to provide structural evidence for 6´-Aminocinchonidine Base by NMR technology: 1H NMR, 13C NMR, 1H-1H COSY, 1H-13C HSQC, 13C-1H HMBC, 1H-1H NOESY, 15N-1H HMBC.

NMR spectra of the structural elucidation can be viewed here: