Quinine (9R, 8S) and Quinidine (9S,8R) are stereoisomers.
I knew we can change the stereochemistry by converting OH into leaving group by MsCl and attack the other side with OH by SN2. But MsCl is expensive so inapplicable for industrial scale.
Another way is converting the 9-OH groups into carbonyl, then the carbonyl intermediates can be epimer (quininon and quinidinone) in equilibrium.
Here is the chemicals i have :
- H2SO4
- HCl
- H2O2
- water
- glacial acetic acid
- NH4OH
- NaOH
- EtOH
- MeOH
i think we can oxidize the OH into carbonyl by using mixtures of H2O2 and acid, but how to reduce the carbonyl? NaBH4 is expensive and the Rabe's synthesis using powdered Al diluted in NaOEt/EtOH by Meerwein-Ponndorf-Verley reduction is also expensive, any other inexpensive substituted metals or reagent i can use to reduce the carbonyl into OH?
I suggested this Industrial Strategy:
Oxidation : React quinine with H₂O₂ and H₂SO₄ to oxidize the 9-OH to quinidinone.
Reduction : Use zinc in acetic acid or HCl to reduce the quinidinone to quinidine (9S,8R).
This method avoids expensive reagents like MsCl, NaBH₄, and the Meerwein-Ponndorf-Verley reduction, relying on more economical zinc as the reducing agent.
Be sure to control the stoichiometry carefully, especially for the oxidation step, to avoid over-oxidation.
You may need to test reaction conditions to optimize yield and stereoselectivity, as the reduction step must yield the 9S,8R stereochemistry of quinidine.
Nicolas Poirier The answer is probably patentable.
M. Raihan Fathurahman Hasbilla Industrial scale means doable and cost effective. Now, you can't file the patent of the process suggested by Nicolas Poirier
a. Photoreduction
Photochemical reduction of the aryl ketones in the presence of sec-butylamine can give the corresponding alcohols.
b. Enzymatic and Microbial reduction
Baker's yeast or T. brockii
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