Potassium Carbonate → Tert-butyl 1,3-dioxoisoindolin-2-yl(2-isopropoxyethyl)carbamate

HRID 220395

Reaktionsgleichung

Reaktionsgleichung von HRID 220395
CS(O[CH2:6][CH2:7][O:8][CH:9]([CH3:11])[CH3:10])(=O)=O.[O:12]=[C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[N:14]1[NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(OCC)(=O)C.O>[O:22]=[C:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13](=[O:12])[N:14]1[N:23]([CH2:6][CH2:7][O:8][CH:9]([CH3:10])[CH3:11])[C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29]

Komponenten

8

Edukt 3

HCID 11430Potassium CarbonateHCID 801162N-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)(tert-butoxy)formamideHCID 184650452-Isopropoxyethyl Methanesulfonate

Produkt 1

HCID 58180589Tert-butyl 1,3-dioxoisoindolin-2-yl(2-isopropoxyethyl)carbamateAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A round bottom flask charged with 2-isopropoxyethyl methanesulfonate (example 77A, 0.791 g, 4.34 mmol) in acetonitrile (21.70 mL) was stirred under an atmosphere of nitrogen. tert-Butyl 1,3-dioxoisoindolin-2-ylcarbamate (1.138 g, 4.34 mmol) was added along with potassium carbonate (2.399 g, 17.36 mmol) and benzyltriethylammonium chloride (0.198 g, 0.868 mmol). The reaction mixture was heated at 50° C. 24 h and cooled to rt over the weekend. The reaction mixture was diluted with ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The combined organics were washed with brine, dried over anhydrous sodium sulfate, vacuum filtered through a plug of silica gel and concentrated in vacuo. The crude oil was used without additional purification (1.26 g, 83% yield).

Aufarbeitung

  1. temperature24 h and cooled to rt over the weekend
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe combined organics were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate, vacuum
  5. filtrationfiltered through a plug of silica gel
  6. concentrationconcentrated in vacuo
  7. customThe crude oil was used without additional purification (1.26 g, 83% yield)

Quellen und Nachweise

ORD-Eintrag
ord-50c7568dcc72409cbf31471272f78f13
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202881B2

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