N,N-Dimethylaniline → (5S)-5-(Aminomethyl)-3-[4-(2-oxo-1-pyrrolidinyl)phenyl]-1,3-oxazolidin-2-one

HRID 1796943

Reaktionsgleichung

Cl[C:2]([O:4][CH2:5][C:6]1C=CC=CC=1)=[O:3].[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:23][CH2:22][CH2:21][C:20]2=[O:24])=[CH:15][CH:14]=1.[CH3:25][N:26](C)C1C=CC=CC=1.C(OCC)(=O)C>O1CCCC1>[NH2:26][CH2:25][C@@H:5]1[O:4][C:2](=[O:3])[N:12]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:23][CH2:22][CH2:21][C:20]3=[O:24])=[CH:15][CH:14]=2)[CH2:6]1

Komponenten

Reaktionsbedingungen

Temperatur: -20 °C

Versuchsvorschrift

At −20° C., benzyl chloroformate (4.27 g, 25.03 mmol) is slowly added dropwise to 1-(4-aminophenyl)pyrrolidin-2-one (4 g, 22.7 mmol) and N,N-dimethylaniline (3.6 ml, 28.4 mmol) in tetrahydrofuran (107 ml). The reaction mixture is stirred at −20° C. for 30 min and then warmed to room temperature. After addition of ethyl acetate (0.5 l), the organic phase is washed with saturated NaCl solution (0.5 l). The combined organic phase are dried (magnesium sulfate), filtered and concentrated under reduced pressure. The residue is titrated with diethyl ether and filtered off with suction. Yield: 5.2 g, 74% of theory, light-beige crystals, melting point: 174° C.

Aufarbeitung

temperaturewarmed to room temperature
washthe organic phase is washed with saturated NaCl solution (0.5 l)
dry with materialThe combined organic phase are dried (magnesium sulfate)
filtrationfiltered
concentrationconcentrated under reduced pressure
filtrationfiltered off with suction

Quellen und Nachweise

ORD-Eintrag: ord-3fb4dbecaf0849ebb432e18ac9688504
Quelldatensatz: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07034017B2

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