Ethyl bromoacetate → Ethyl 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetate

HRID 1667062

Reaktionsgleichung

[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][CH2:10][NH:9][C:8]2=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>O1CCCC1>[O:12]=[C:8]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:11][CH2:10][N:9]1[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a solution of the product from Example 1A (1.0 g, 4.21 mmol) in tetrahydrofuran (20 mL) was added potassium tert-butoxide (1.0 M in tetrahydrofuran, 6.3 mL, 6.3 mmol) via syringe under nitrogen followed by ethyl 2-bromoacetate (0.47 mL, 4.21 mmol). The reaction mixture was heated to 80° C. and stirred overnight. The reaction mixture was cooled to room temperature, concentrated, and then diluted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography eluting with ethyl acetate/hexane (20:80) gave the title compound. MS (DCI+) m/z 324.2 (M+H)+.

Aufarbeitung

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated
additiondiluted with ethyl acetate
washThe organic layer was washed with water and brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
washSilica gel chromatography eluting with ethyl acetate/hexane (20:80)

Quellen und Nachweise

ORD-Eintrag: ord-6a398c54018d42c0afc91cbb7161086d
Quelldatensatz: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08044069B2

Verknüpfte Notizen

Wird geladen…