Acetic Acid → 2-[2-(Pyrrolidin-1-yl)ethylthio]methyl-3,5-dicarboethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine

HRID 358989

Reaktionsgleichung

Reaktionsgleichung von HRID 358989
Cl.[N:2]1([CH2:7][CH2:8]Cl)[CH2:6][CH2:5][CH2:4][CH2:3]1.[SH:10][CH2:11][C:12]1[NH:13][C:14]([CH3:37])=[C:15]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:16]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=2)[C:17]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19].[O-]CC.[Na+].CC(O)=O>C(O)C>[N:2]1([CH2:7][CH2:8][S:10][CH2:11][C:12]2[NH:13][C:14]([CH3:37])=[C:15]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:16]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=3)[C:17]=2[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:6][CH2:5][CH2:4][CH2:3]1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 2723922Sodium ethoxideHCID 116758332-Mercaptomethyl-3,5-dicarboetoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine

Produkt 1

HCID 198311862-[2-(Pyrrolidin-1-yl)ethylthio]methyl-3,5-dicarboethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridineAusbeute 41,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 2-(pyrrolidin-1-yl)-1-chloroethane hydrochloride (2.8 g), 2-mercaptomethyl-3,5-dicarboethoxy-4-(m-nitrophenyl) -6-methyl-1,4-dihydropyridine (5.4 g) and sodium ethoxide (2 g) in ethanol (70 ml) is heated to the reflux temperature for 6 hours, then it is neutralized with AcOH and evaporated under reduced pressure. The residue, after the usual work-up, is purified by column-chromatography (SiO2 ; 210 g; eluent AcOH/MeOH 99/1) to give 2.8 g of 2-[2-(pyrrolidin-1-yl)ethylthio]methyl-3,5-dicarboethoxy-4-(m-nitrophenyl) -6-methyl-1,4-dihydropyridine, as an oil, that upon treatment with fumaric acid gives the corresponding salt, m.p. 192°-194° C.

Aufarbeitung

  1. customevaporated under reduced pressure
  2. customThe residue, after the usual work-up, is purified by column-chromatography (SiO2 ; 210 g; eluent AcOH/MeOH 99/1)

Quellen und Nachweise

ORD-Eintrag
ord-8228bc68d1484fdaa0c278a4d67104d6
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US04999362

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