Reaktion #80736

Reaktionsgleichung

3-nitrobenzaldehyde

1-benzyl-3-acetoacetoxypyrrolidine

3-aminocrotonic acid methyl ester

→

2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(1-benzylpyrrolidin-3-yl)ester 5-methyl ester

Ausbeute 99.9%

Lösungsmittel

isopropanol

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe solution thus obtained
2. 2
   Temperaturwas refluxed for 8 hours
3. 3
   workup.DISTILLATIONThen, the solvent was distilled off under reduced pressure
4. 4
   Sonstigethe residue thus formed
5. 5
   Waschenthe solution was washed, in succession, with diluted hydrochloric acid, water
6. 6
   Trocknena saturated aqueous sodium hydrogencarbonate solution, and dried over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONThen, the solvent was distilled off under reduced pressure

Vorschrift

In 5 ml of isopropanol were dissolved 1.51 g (0.01 mole) of 3-nitrobenzaldehyde, 2.61 g (0.01 mole) of 1-benzyl-3-acetoacetoxypyrrolidine, and 1.15 g (0.01 mole) of 3-aminocrotonic acid methyl ester and the solution thus obtained was refluxed for 8 hours. Then, the solvent was distilled off under reduced pressure, the residue thus formed was dissolved in chloroform, the solution was washed, in succession, with diluted hydrochloric acid, water, a saturated aqueous sodium hydrogencarbonate solution, and dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure to provide 4.91 g of 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(1-benzylpyrrolidin-3-yl)ester 5-methyl ester as a caramel form.

Quelle