Tetrabutylammonium Fluoride → methyl 3-[(2S)-2-methylpyrrolidin-1-yl]-2-(1H-pyrrol-3-yl)quinoxaline-6-carboxylate

HRID 1403474Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1403474
[CH3:1][C@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[C:8]([C:21]2[CH:25]=[CH:24][N:23]([Si](C(C)C)(C(C)C)C(C)C)[CH:22]=2)=[N:9][C:10]2[C:15]([N:16]=1)=[CH:14][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:11]=2.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][C@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[C:8]([C:21]2[CH:25]=[CH:24][NH:23][CH:22]=2)=[N:9][C:10]2[C:15]([N:16]=1)=[CH:14][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:11]=2

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 70665097methyl 3-[(2S)-2-methylpyrrolidin-1-yl]-2-[1-[tris(propan-2-yl)silyl]-1H-pyrrol-3-yl]quinoxaline-6-carboxylate

Produkt 1

HCID 70664801methyl 3-[(2S)-2-methylpyrrolidin-1-yl]-2-(1H-pyrrol-3-yl)quinoxaline-6-carboxylateAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl 3-[(2S)-2-methylpyrrolidin-1-yl]-2-[1-[tris(propan-2-yl)silyl]-1H-pyrrol-3-yl]quinoxaline-6-carboxylate (150 mg, 0.30 mmol) in tetrahydrofuran (30 ml) was added Tetra-n-butylammonium fluoride (TBAF) (80 mg, 0.31 mmol) with stirring for 10 min at room temperature. The reaction was then quenched with water (10 ml). The resulting solution was extracted with dichloromethane (3×10 ml) and the organic layers combined and dried over anhydrous magnesium sulfate, concentrated under vacuum to afford methyl 3-[(2S)-2-methylpyrrolidin-1-yl]-2-(1H-pyrrol-3-yl)quinoxaline-6-carboxylate as a light yellow solid (100 mg, 98%).

Aufarbeitung

  1. customThe reaction was then quenched with water (10 ml)
  2. extractionThe resulting solution was extracted with dichloromethane (3×10 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-e5e98a2862b44472a4e42c5e9dafb58d
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912188B2

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