Water → HCID 67759194, Verbindung

HRID 1590182Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1590182
[CH3:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][CH:7]([CH2:20][C:21]([O:23]C2C=CC([N+]([O-])=O)=CC=2)=O)[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[O:9])=[CH:4][CH:3]=1.[CH2:35]1[C@@H:43]2[C@@H:38]([CH2:39][CH:40]=[CH:41][CH2:42]2)[CH2:37][NH:36]1.O>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]([CH2:20][C:21]([N:36]2[CH2:37][C@H:38]3[C@H:43]([CH2:42][CH:41]=[CH:40][CH2:39]3)[CH2:35]2)=[O:23])[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[O:9])=[CH:33][CH:34]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 16765331cis-2,3,3a,4,7,7a-Hexahydro-1h-isoindoleHCID 54101102Di(4-nitrophenyl) 2-(4-methylbenzyl)succinate

Produkt 1

HCID 67759194HCID 67759194, VerbindungAusbeute 75,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of di(4-nitrophenyl) 2-(4-methylbenzyl)succinate (2.4 g) in N,N-dimethylformamide (30 ml) was added a solution of cis-3a,4,7,7a-tetrahydroisoindoline (0.62 g) in N,N-dimethylformamide (10 ml) with stirring at 0° C. After stirring at 0° C. for 3 hours, water was added to the reaction mixture and extracted with ethyl acetate. The organic layer was washed successively with three 1N sodium hydroxide solutions, 1N-hydrochloric acid, and brine and dried over MgSO4. After the solvent was evaporated under reduced pressure, the residue was recrystallized from hexane-ethyl acetate (4:1) to give 1.7 g of 4-nitrophenyl 2-(4-methylbenzyl)-3-(cis-3a,4,7,7a-tetrahydro-2-isoindolinylcarbonyl)propionate.

Aufarbeitung

  1. stirringAfter stirring at 0° C. for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed successively with three 1N sodium hydroxide solutions, 1N-hydrochloric acid, and brine
  4. dry with materialdried over MgSO4
  5. customAfter the solvent was evaporated under reduced pressure
  6. customthe residue was recrystallized from hexane-ethyl acetate (4:1)

Quellen und Nachweise

ORD-Eintrag
ord-7b28c7cc36484117ae7bd9474efd1241
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05202335

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