Triethylamine → (R)-N,N-Dimethyl-1-(4-nitro-2-(trifluoromethyl)benzyl)pyrrolidin-3-amine
Reaktionsgleichung
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[C:12]([F:15])([F:14])[F:13].CCN(CC)CC.[CH3:23][N:24]([CH3:30])[C@@H:25]1[CH2:29][CH2:28][NH:27][CH2:26]1>C(Cl)Cl>[CH3:23][N:24]([CH3:30])[C@@H:25]1[CH2:29][CH2:28][N:27]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=2[C:12]([F:15])([F:14])[F:13])[CH2:26]1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of crude 1-(bromomethyl)-4-nitro-2-(trifluoromethyl)benzene (17.5 mmol, 75% pure) in 40 mL of DCM was added Et3N (2.69 mL, 19.3 mmol) and (R)-(+)-3-(dimethylamino)pyrrolidine (2.0 g, 17.5 mmol). After stirring overnight at ambient temperature under an atmosphere of N2, the reaction solution was concentrated, added aq. NaHCO3 (100 mL), and the resulting mixture extracted with DCM (4×50 mL). The combined organic layer was dried over Na2SO4, filtered, concentrated, and the resulting residue was purified by silica gel chromatography (eluted with 0-10% MeOH/DCM) to provide 3.35 g of product as a yellow oil.
Aufarbeitung
- concentrationthe reaction solution was concentrated
- additionadded aq. NaHCO3 (100 mL)
- extractionthe resulting mixture extracted with DCM (4×50 mL)
- dry with materialThe combined organic layer was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customthe resulting residue was purified by silica gel chromatography (eluted with 0-10% MeOH/DCM)
Quellen und Nachweise
- ORD-Eintrag
- ord-4eab272562e14da8bf3f28a8c5ab190f
- Quelldatensatz
- uspto-grants-2013_06
- Patentnummer
- US08470851B2
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