Water → (4R)-5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	(S)-[(2R,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol	HCID 5953	—
Reactant	2,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl ester	HCID 173322	—
Solvent	Methanol	HCID 887	—
Product	(4R)-5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid	HCID 748472	18.6%

Reaction Conditions

Temperature	90 °C

Reaction Steps

To a solution of 5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (700 g, 2.1 mol) in methanol (14 L) was added Quinidine (617 g, 1.90 mol). The mixture was stirred at 90° C. under reflux until Quinidine was completely dissolved. The stirring was continued for 3 hours. 4.5 L water was added. The stirring was continued for 0.5 hour. The mixture was cooled down slowly. A solid was precipitated out and was filtered. The filter cake was treated with hydrochloric acid to produce (R)-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (130 g) in a yield of 18.6%.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09198902B2
Source dataset	uspto-grants-2015_12
ORD ID	ord-ec683ddeacb940b4bb3a07bfcc9f3f0b
Source note	uspto-grants-2015_12