Morpholine → Tert-butyl 2-(6-morpholino-2,3-dioxoindolin-1-yl)acetate

HRID 571262Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 571262
F[C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:20])[C:7](=[O:19])[N:8]2[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:4][CH:3]=1.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C(OCC)(=O)C>CS(C)=O>[O:24]1[CH2:25][CH2:26][N:21]([C:2]2[CH:10]=[C:9]3[C:5]([C:6](=[O:20])[C:7](=[O:19])[N:8]3[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:4][CH:3]=2)[CH2:22][CH2:23]1

Komponenten

5

Edukt 3

HCID 8083MorpholineHCID 8857Ethyl AcetateHCID 86681676Tert-butyl 2-(6-fluoro-2,3-dioxoindolin-1-yl)acetate

Produkt 1

HCID 86681677Tert-butyl 2-(6-morpholino-2,3-dioxoindolin-1-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 2-(6-fluoro-2,3-dioxoindolin-1-yl)acetate (0.400 g, 1.432 mmol) in DMSO (10 ml), morpholine (1.248 ml, 14.32 mmol) was added drop wise at room temperature. The resulting orange mixture was stirred at room temperature for 24 hours. Ethyl acetate (50 ml) was added and the solution was washed with brine (3×30 ml); the organic phase was dried over sodium sulfate, filtered and concentrated under vacuum. The crude was purified by silica gel flash chromatography (DCM:MeOH=98:2) affording tert-butyl 2-(6-morpholino-2,3-dioxoindolin-1-yl)acetate (0.400 g, 1.155 mmol, 81% yield 0. MS/ESI+ 347.1 [MH]+.

Aufarbeitung

  1. washthe solution was washed with brine (3×30 ml)
  2. dry with materialthe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe crude was purified by silica gel flash chromatography (DCM:MeOH=98:2)

Quellen und Nachweise

ORD-Eintrag
ord-a999c0ff7beb4415972f24b4fdd5a4f5
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09024027B2

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