Methyl iodide → 1-Benzyl 3-methyl 3-methylpyrrolidine-1,3-dicarboxylate
Reaktionsgleichung
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:11][C:12]1([C:27]([O-:29])=[O:28])[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:13]1.[CH3:30]I.[Cl-].[NH4+]>C1COCC1>[CH3:11][C:12]1([C:27]([O:29][CH3:30])=[O:28])[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:13]1Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
Lithium bis(trimethylsilyl)amide (16.4 mL, 16.4 mmol) was added to 1-benzyl 3-methylpyrrolidine-1,3-dicarboxylate (3.45 g, 13.1 mmol) in THF (20 mL) at −78° C., and the reaction was stirred at −78° C. for 20 minutes. MeI (1.10 mL, 17.7 mmol) was added, and the reaction was warmed to room temperature. After 2 hours at room temperature, the mixture was poured onto saturated ammonium chloride (20 mL), extracted with ether, washed with brine and dried over sodium sulfate. After removal of the solvent, the residue was purified by chromatography (hexane:ethyl acetate, 4:1) to give 1-benzyl 3-methyl 3-methylpyrrolidine-1,3-dicarboxylate (2.72 g, 75% yield) as an oil.
Aufarbeitung
- temperaturethe reaction was warmed to room temperature
- waitAfter 2 hours at room temperature
- extractionextracted with ether
- washwashed with brine
- dry with materialdried over sodium sulfate
- customAfter removal of the solvent
- customthe residue was purified by chromatography (hexane:ethyl acetate, 4:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-6c153044c92842159d561f886a96ca6d
- Quelldatensatz
- uspto-grants-2013_10
- Patentnummer
- US08545897B2
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