Reaktion #45907

Reaktionsgleichung

sodium hydride

Methyl iodide

tert-butyl 5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate

citric acid

sodium hydride

→

compound

Ausbeute 36.0%

tert-Butyl(3S)-3-methyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate

Ausbeute 36.0%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGby stirring at room temperature for 13 hours
2. 2
   workup.ADDITIONwas added to the reaction liquid
3. 3
   Extraktionfollowed by extraction with ethyl acetate
4. 4
   WaschenThe organic layer was washed with saturated brine
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   Sonstigethe solvent was evaporated away
7. 7
   SonstigeThe resulting residue was separated
8. 8
   Sonstigepurified by silica gel column chromatography (eluent, n-hexane

Vorschrift

Methyl iodide (21.8 ml, 0.35 mol) was added to an N,N-dimethylformamide (150 ml) solution of tert-butyl 5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate (I-341) (20.28 g, 70.1 mmol), then at room temperature, sodium hydride (55%, w/w) (1 g) was added, followed by stirring as such. Afterwards, sodium hydride (1.9 g, 2.7 g, 2.79 g, 1.97 g) was successively added, followed by stirring at room temperature for 13 hours. With cooling with ice, aqueous 10% citric acid solution was added to the reaction liquid, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated away. The resulting residue was separated and purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=3:1, v/v) to obtain the entitled compound (7.65 g, 36%).

Quelle