Quincoridine (QCD) – Fine Chemical

Introduction

Quincoridine (QCD) (CAS-No. 207129-36-0) is an enantiopure quinuclidine compound, which can be obtained by a chemical transformation of Cinchona alkaloids.

Quinuclidine compounds are known to have a high affinity towards various receptors (5-HT₃, 5-HT₄, NK₁…).

For this reason they have high potential in the treatment of different diseases such as alzheimer, arteriosclerosis, inflammatory diseases / allergies (hay fever, eczema), bronchitis, high cholesterol levels, urinary incontinence, cancer etc.

For instance the top-selling drug Solifenacin is a competitive muscarinic receptor agonist, which is used in the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency, and urinary frequency.

Newly developed QCI- and QCD-derivatives provide access to more complex and selective therapeutic agents which are also enantiomerically pure.

The additional hydroxymethyl functionality of Quincorine (QCI) and Quincoridine (QCD) and their derivatives allows attachment of further pharmacophoric groups and prodrugs.

Combinatorial techniques and high throughput screening will facilitate further developments in pharmacology and catalysis. Apart from their biological activity the class of substances has been used increasingly in other molecular recognition processes, especially for developing efficient phase transfer catalysts and transition metal mediated reactions.

Asymmetric catalysts

 The asymmetric dihydroxylation and enolate alkylation reflect the remarkable versatility of the Cinchona alkaloids (K. B. Sharpless and E. J. Corey). QCI- and QCD-derivatives open a path to a wide variety of non-natural and semi-natural Cinchona alkaloids.

The demand of enantioselective catalyst is steadily increasing. Therefore a new class of chiral ligands based on the quinuclidines QCI- and QCD have been developed, which turned out to be highly enantioselective in asymmetric synthesis. Values up to 99 % ee could be obtained for different catalytic processes, like acylation (Chem.Commun. 2004,1548) , hydrogenation (Per. I. Arvidson. Org. Biomol. Chem, 2003, 1) or cross coupling reactions.

Similarly, a series of new chiral building blocks has been developed expanding the chiral pool of fine chemicals (Org. Lett. 1999, 1, 1607; J.Org. Chem. 2000, 65, 3982; Org. Lett. 2000, 2, 1661, Eur. J. Org. Chem. 2003, 3784-3790, Eur. J. Org. Chem. 2004, 4293-4312).

Physical properties

Quincoridine (QCD) (CAS-No. 207129-36-0) is a clear oil at room temperature. The boiling point is 267 °C. Quincoridine should be stored at – 10 °C.

Synonyms

(2R,4S,5R)-2-Hydroxymethyl-5-vinyl-quinuclidine