Morpholine → [1-(3-Morpholin-4-yl-phenyl)ethyl]carbamic acid tert-butyl ester
Reaktionsgleichung
[C:1]([O:5][C:6]([NH:8][CH:9]([C:11]1[CH:12]=[C:13](OS(C(F)(F)F)(=O)=O)[CH:14]=[CH:15][CH:16]=1)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>ClCCl>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[CH:12]=1)[CH3:10])([CH3:4])([CH3:3])[CH3:2]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
A mixture of trifluoro-methanesulfonic acid 3-(1-tert-butoxycarbonylaminoethyl)phenyl ester (1.5 g, 4.08 mmol), morpholine (8 mL) Pd2(dba)3 (187 mg, 5 mol %), di-t-butyl-biphenylphosphine (243 mg, 20 mol %), potassium phosphate (1.21 g, 5.71 mmol) was stirred at 80° C. in a sealed tube for 10 hours. After cooling down, the reaction mixture was diluted with dichloromethane (50 mL) and washed with water (10 mL). The aqueous layer was extracted with dichloromethane (2×15 mL) and the combined organic layer was dried over magnesium sulfate and concentrated under vacuum. The crude product was purified by flash chromatography of Biotage with 30% ethyl acetate/hexanes to provide the title compound as a pale yellow solid (1.01 g, 81% yield).
Aufarbeitung
- temperatureAfter cooling down
- washwashed with water (10 mL)
- extractionThe aqueous layer was extracted with dichloromethane (2×15 mL)
- dry with materialthe combined organic layer was dried over magnesium sulfate
- concentrationconcentrated under vacuum
- customThe crude product was purified by flash chromatography of Biotage with 30% ethyl acetate/hexanes
Quellen und Nachweise
- ORD-Eintrag
- ord-bc23ea6c09be49498922e6282e198ea3
- Quelldatensatz
- uspto-grants-2004_12
- Patentnummer
- US06831080B2
Notizen zur Reaktion
Wird geladen…