2-(N-Benzyl-N-methylamino)ethyl 3-amino-2-butenoate → 2-(N-benzyl-N-methylamino)ethyl 2,6-dimethyl-4-(3-nitrophenyl)-5-(2-oxo-1,3,2-dioxaphosphorinan-2-yl)-1,4-dihydropyridine-3-carboxylate

HRID 1087643Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1087643
[N+:1]([C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[CH:7]=[C:8]([P:12]1(=[O:18])[O:17][CH2:16][CH2:15][CH2:14][O:13]1)[C:9]([CH3:11])=O)([O-:3])=[O:2].[CH2:22]([N:29]([CH2:31][CH2:32][O:33][C:34](=[O:39])/[CH:35]=[C:36](\[NH2:38])/[CH3:37])[CH3:30])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)(C)C>[CH3:37][C:36]1[NH:38][C:9]([CH3:11])=[C:8]([P:12]2(=[O:18])[O:17][CH2:16][CH2:15][CH2:14][O:13]2)[CH:7]([C:6]2[CH:19]=[CH:20][CH:21]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:35]=1[C:34]([O:33][CH2:32][CH2:31][N:29]([CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH3:30])=[O:39]

Komponenten

4

Edukt 2

HCID 125291882-(N-Benzyl-N-methylamino)ethyl 3-amino-2-butenoateHCID 540679512-(1-(3-Nitrobenzylidene)acetonyl)-2-oxo-1,3,2-dioxaphosphorinane

Produkt 1

HCID 136045572-(N-benzyl-N-methylamino)ethyl 2,6-dimethyl-4-(3-nitrophenyl)-5-(2-oxo-1,3,2-dioxaphosphorinan-2-yl)-1,4-dihydropyridine-3-carboxylateAusbeute 59,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A mixture of 3.11 grams of 2-(1-(3-nitrobenzylidene)-acetonyl)-2-oxo-1,3,2-dioxaphosphorinane and 2.48 grams of 2 -(N-benzyl-N-methylamino)ethyl3-aminocrotonate was dissolved in 30 ml of isopropanol and the mixture was heated to reflux for eight hours. The reaction solution was concentrated in vacuo and the residue was purified by subjecting to a column chromatography (silica gel, n-hexane-ethyl acetate). The resulting pale yellow oil (3.8 grams) was crystallized with ether and recrystallized from a mixture of ethyl acetate and ether to give 3.2 grams of 2-(N-benzyl-N-methylamino)ethyl 2,6-dimethyl-4-(3-nitrophenyl)-5-(2-oxo-1,3,2-dioxaphosphorinan- 2-yl)-1,4-dihydropyridine-3-carboxylate, pale yellow crystals, m.p. 139°-40° C.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for eight hours
  3. concentrationThe reaction solution was concentrated in vacuo
  4. customthe residue was purified
  5. customThe resulting pale yellow oil (3.8 grams) was crystallized with ether
  6. customrecrystallized from a mixture of ethyl acetate and ether

Quellen und Nachweise

ORD-Eintrag
ord-cebe0f14f78043ea8b0bbe32e27dc24b
Quelldatensatz
uspto-grants-1991_07
Patentnummer
US05036059

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