252056-58-9

Basic information

• Product Name: 1,3(4H)-Pyridinedicarboxylic acid, 4-(4-fluorophenyl)-5,6-dihydro-, dimethyl ester
• CAS NO: 252056-58-9
• Molecular Formula: C15H16FNO4
• Molecular Weight: 293.295
• Mol File: 252056-58-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1,3(4H)-Pyridinedicarboxylic acid, 4-(4-fluorophenyl)-5,6-dihydro-, dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3(4H)-Pyridinedicarboxylic acid, 4-(4-fluorophenyl)-5,6-dihydro-, dimethyl ester(252056-58-9)
• EPA Substance Registry System: 1,3(4H)-Pyridinedicarboxylic acid, 4-(4-fluorophenyl)-5,6-dihydro-, dimethyl ester(252056-58-9)

Safety Data

• Hazardous Substances Data: 252056-58-9(Hazardous Substances Data)

Upstream product

• 459-45-0 4-fluorobenzenediazonium tetrafluoroborate 
• 76508-76-4 N-methoxycarbonyl-3-carboxymethyl-1,2,5,6-tetrahydropyridine 
• 955998-65-9 methyl 4-(4-fluorophenyl)-1,4,5,6-tetrahydropyridine-3-carboxylate 
• 79-22-1 methyl chloroformate 
• 57611-47-9 1-benzyl-4-oxo-piperidine-3-carboxylic acid methyl ester 
• 793-19-1 bis(2-methoxycarbonylethyl)benzylamine 
• 139372-09-1 prop-2-ynylcarbamic acid methyl ester 
• 252056-57-8 1,3-bis(methoxycarbonyl)-4-(4-fluorophenyl)-1,4-dihydropyridine 
• 93-60-7 methyl 3-pyridinecarboxylate 
• 211511-68-1 N-methoxycarbonyl-3-hydroxymethyl-1,2,5,6-tetrahydropyridine 
• 88928-69-2 1-benzyl-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester 
• 955998-64-8 methyl 1-benzyl-4-hydroxypiperidine-3-carboxylate 

Downstream Products

• 61869-08-7 (+/-)-trans-paroxetine 

Relevant articles and documents

Substrate Control in the Gold(I)-Catalyzed Cyclization of β-Propargylamino Acrylic Esters and Further Transformations of the Resultant Dihydropyridines

N-Protected β-propargylamino acrylic esters with a push-pull olefinic bond afforded good to high yields of dihydropyridines upon treatment with 5% tris(2-furyl)phosphine-gold(I) chloride/silver(I) tetrafluoroborate [(TFP)AuCl/AgBF4] in anhydrous benzene. Carbamate and sulfonyl groups were employed for nitrogen protection. On a model enyne, the p-methoxybenzenesulfonyl (MBS) group was found to be a better protective group than tosyl in terms of cyclization yield, and also the yield of elimination to the corresponding 2,3,4-trisubstituted pyridines. Boc-protected dihydropyridines underwent partial deprotection/oxidation under the cyclization conditions, which enabled a more straightforward, one-pot preparation of the corresponding pyridines. In another application, an appropriately substituted derivative protected as a stable methoxycarbamate was subjected to catalytic hydrogenation affording the known precursor of paroxetine. The chemoselectivity of enyne cyclization (dihydropyridine vs. pyrrole) is governed, among other factors, by C-3 substitution. Dihydropyridines were obtained as sole products regardless of the catalyst/conditions when C-3 was unsubstituted. (Figure presented.).

Efficient Heck arylations of cyclic and acyclic acrylate derivatives using arenediazonium tetrafluoroborates. A new synthesis of the antidepressant drug (±)-paroxetine

The Heck arylation of acyclic- and cyclic-substituted acrylates using several arenediazonium tetrafluoroborates was investigated. Arylations were carried out under aerobic, ligand-free conditions to provide the corresponding substituted acrylates in moderate to high isolated yields. Heck arylations were usually completed in less than 2 h in refluxing methanol. The aza-endocyclic acrylate derivative 11a was converted into the antidepressant drug (±)-paroxetine in a concise new route in good overall yield.