6´-Aminocinchonine Base – Fine Chemical

6´-Aminocinchonine Base (CAS-No. 2143936-31-4) 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´-Aminocinchonine Base (CAS-No. 2143936-31-4) is a beige to pink, crystalline powder or it consists of fine, colourless needles, being soluble in methanol. The melting point is in the range of 118 -129 °C. This compound is not hygroscopic and contains less than 5.0 % water. 6`-Amonocinchonine could be stored at ambient conditions in well-closed, light-resistant containers.

Synonyms

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

NMR spectra of the structural elucidation can be viewed here: