Perfluoro-1-butanesulfonyl fluoride → HCID 118045501, Verbindung
Reaktionsgleichung
O[CH2:2][C@@H:3]([N:10]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.F.F.F.C(N(CC)CC)C.[F:31]C(F)(S(F)(=O)=O)C(F)(F)C(F)(F)C(F)(F)F.CCN(C(C)C)C(C)C>C1(C(F)(F)F)C=CC=CC=1>[F:31][CH2:2][C@@H:3]([N:10]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of (S)-2-(2-hydroxy-1-phenylethyl)isoindoline-1,3-dione (1.5 g, 5.61 mmol) in PhCF3 (18.71 mL) was added triethylamine trihydrofluoride (5.48 mL, 33.7 mmol), perfluorobutanesulfonyl fluoride (1.019 mL, 5.67 mmol), DIEA (14.70 mL, 84 mmol) at room temperature. The reaction mixture was stirred at room temperature for 1 h, then more perfluorobutanesulfonyl fluoride (1.019 mL, 5.67 mmol) was added. After 5 h, the reaction mixture was quenched with NaHCO3 and extracted with EtOAc. The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate, filtered off, and concentrated in vacuo. The crude product was purified by flash chromatography (0-10% EtOAC in heptane) yielding (S)-2-(2-fluoro-1-phenylethyl)isoindoline-1,3-dione (30% yield). LCMS (m/z): 270.1 (MH+), 0.96 min.
Aufarbeitung
- waitAfter 5 h
- customthe reaction mixture was quenched with NaHCO3
- extractionextracted with EtOAc
- washThe combined organic layers were washed with water and brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered off
- concentrationconcentrated in vacuo
- customThe crude product was purified by flash chromatography (0-10% EtOAC in heptane)
Quellen und Nachweise
- ORD-Eintrag
- ord-ea4caffecdc04c22826c17e1a1919dbf
- Quelldatensatz
- uspto-grants-2016_01
- Patentnummer
- US09242996B2
Notizen zur Reaktion
Wird geladen…