tert-Butyl 2-(4-(bromomethyl)phenyl)-2-cyclopentylacetate → tert-Butyl cyclopentyl{4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}acetate
Reaktionsgleichung
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:17][CH:16]=1>CN(C=O)C>[CH:29]1([CH:21]([C:18]2[CH:19]=[CH:20][C:15]([CH2:14][N:5]3[C:1](=[O:11])[C:2]4[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:4]3=[O:6])=[CH:16][CH:17]=2)[C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[CH2:33][CH2:32][CH2:31][CH2:30]1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
Under argon, 6.49 g (35 mmol) of potassium phthalimide were initially charged in 60 ml of DMF, 15 g (31.8 mmol) of tert-butyl(+/−)-2-(4-(bromomethyl)phenyl)-2-cyclopentylacetate were added and the mixture was stirred at 80° C. overnight. A further 0.5 equivalent of potassium phthalimide was then added, and the mixture was stirred at 80° C. for another 6 h. The reaction mixture was then filtered, and the filtrate was concentrated under reduced pressure. The residue was triturated with ethanol and the solid was filtered off with suction, washed with ethanol and dried under high vacuum. This gave 8.5 g (about 96% pure, 61% of theory) of the target compound.
Aufarbeitung
- stirringthe mixture was stirred at 80° C. for another 6 h
- filtrationThe reaction mixture was then filtered
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue was triturated with ethanol
- filtrationthe solid was filtered off with suction
- washwashed with ethanol
- customdried under high vacuum
Quellen und Nachweise
- ORD-Eintrag
- ord-a607e56ac90f428fbb4cc64d3a909d68
- Quelldatensatz
- uspto-grants-2015_03
- Patentnummer
- US08987256B2
Notizen zur Reaktion
Wird geladen…