Ethyl bromoacetate → Ethyl 2-(3,3-bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl)acetate
Reaktionsgleichung
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[CH2:12][CH2:11][NH:10][C:9]2=[O:13])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]>O1CCCC1>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:8]2([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:12][CH2:11][N:10]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:9]2=[O:13])=[CH:15][CH:16]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
To a solution of the product from Example 58B (0.82 g, 3.00 mmol) in tetrahydrofuran (20 mL) was added potassium tert-butoxide (1.0 M in tetrahydrofuran, 4.5 mL, 4.5 mmol) via syringe under nitrogen followed by ethyl 2-bromoacetate (0.33 mL, 3.00 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 reaction mixture was washed with water and brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified with silica gel chromatography eluting with ethyl acetate/hexane (20:80) gave the title compound. MS (APCI+) m/z 359.9 (M+H)+.
Aufarbeitung
- temperatureThe reaction mixture was cooled to room temperature
- concentrationconcentrated
- additiondiluted with ethyl acetate
- washThe reaction mixture was washed with water and brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified with silica gel chromatography
- washeluting with ethyl acetate/hexane (20:80)
Quellen und Nachweise
- ORD-Eintrag
- ord-ddedb08011fb42c98960fdd27a629f3b
- Quelldatensatz
- uspto-grants-2011_10
- Patentnummer
- US08044069B2
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