Cesium carbonate → (S)-5-Oxo-1-(6-trifluoromethyl-pyridin-3-yl)-pyrrolidine-2-carboxylic acid tert-butyl ester

HRID 469743

Reaktionsgleichung

C(=O)([O-])[O-].[Cs+].[Cs+].C(OC(C1CCCCC1=O)=O)C.[C:19]([O:23][C:24]([C@@H:26]1[CH2:30][CH2:29][C:28](=[O:31])[NH:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].Br[C:33]1[CH:34]=[CH:35][C:36]([C:39]([F:42])([F:41])[F:40])=[N:37][CH:38]=1>CS(C)=O.[Cu](Br)Br>[C:19]([O:23][C:24]([C@@H:26]1[CH2:30][CH2:29][C:28](=[O:31])[N:27]1[C:33]1[CH:38]=[N:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

A solution of cesium carbonate (1.539 g; 4.725 mmol), copper bromide (0.032 g; 0.225 mmol) and ethyl-2-oxocyclohexanecarboxylate (0.072; 0.45 mmol) in anhydrous dimethyl sulfoxide (1.25 mL) is degassed with argon and stirred 30 minutes. To this solution is added (S)-5-oxo-pyrrolidine-2-carboxylic acid tert-butyl ester (0.5 g; 2.699 mmol) and 5-bromo-2-trifluoromethylpyridine (0.508 g; 2.25 mmol) in 1 mL anhydrous dimethyl sulfoxide. The mixture is heated in a sealed tube to 60° C. in an oil bath and stirred overnight. The reaction mixture is cooled to room temperature, filtered through Celite® and washed with ethyl acetate. The combined organics are washed with brine, dried over sodium sulfate and concentrated under reduced pressure. ESI m/z 331 [M+H]+

Aufarbeitung

stirringstirred overnight
temperatureThe reaction mixture is cooled to room temperature
filtrationfiltered through Celite®
washwashed with ethyl acetate
washThe combined organics are washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-1ad5e847892741e98901bd738e33beba
Quelldatensatz: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08629157B2

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