Methyl iodide → 1-Benzyl 3-methyl 3-methylpyrrolidine-1,3-dicarboxylate

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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]1

Komponenten

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-17c05f7dd96043e9b6486a38064e2514
Quelldatensatz: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08758830B2

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