Ammonium Chloride → 1-Cyclohexyl-3-(2,6-dichloro-4-methoxy-benzyl)-pyrrolidin-2-one

HRID 415977

Reaktionsgleichung

[CH:1]1([N:7]2[CH2:11][CH2:10][CH2:9][C:8]2=[O:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].CC([N-]C(C)C)C.Br[CH2:22][C:23]1[C:28]([Cl:29])=[CH:27][C:26]([O:30][CH3:31])=[CH:25][C:24]=1[Cl:32].[Cl-].[NH4+]>O1CCCC1>[CH:1]1([N:7]2[CH2:11][CH2:10][CH:9]([CH2:22][C:23]3[C:24]([Cl:32])=[CH:25][C:26]([O:30][CH3:31])=[CH:27][C:28]=3[Cl:29])[C:8]2=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

Dissolve commercially available 1-cyclohexyl-pyrrolidin-2-one (88.2 g, 527.9 mmol) in 2500 mL tetrahydrofuran and cool to −78° C. Add 176 mL 2 M LDA and stir for ˜5 min. Add 2-bromomethyl-1,3-dichloro-5-methoxy-benzene (95 g, 351.9 mmol) and allow the reaction to warm to room temperature. Pour the mixture into saturated ammonium chloride and extract twice with dichloromethane. Dry over sodium sulfate, filter and concentrate under vacuum to obtain a tan solid. Add hexanes and stir rapidly before filtering. Wash the filter cake several times with cold hexane to obtain 86 g (69%) of a light-tan solid: MS (m/z): 356 (M+).

Aufarbeitung

customthe reaction
temperatureto warm to room temperature
extractionextract twice with dichloromethane
dry with materialDry over sodium sulfate
filtrationfilter
concentrationconcentrate under vacuum
customto obtain a tan solid
filtrationbefore filtering
washWash the filter cake several times with cold hexane

Quellen und Nachweise

ORD-Eintrag: ord-671ed090c526489ea143d527e9a47bc2
Quelldatensatz: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08088776B2

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