Hydrochloric Acid → 3-Fluoro-N-(5-methylaminomethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzenesulfonamide
Reaktionsgleichung
[F:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[CH:21]=[CH:20][C:19]3[CH:18]([CH2:22][NH:23][CH:24]=O)[CH2:17][CH2:16][CH2:15][C:14]=3[CH:13]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.B.C1COCC1.Cl>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[CH:21]=[CH:20][C:19]3[CH:18]([CH2:22][NH:23][CH3:24])[CH2:17][CH2:16][CH2:15][C:14]=3[CH:13]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 23 °C
Versuchsvorschrift
To a solution of 0.17 grams (0.469 mmoles) 3-fluoro-N-(5-formylaminomethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzenesulfonamide in 5 mL THF was added 2 mL 1.0M borane-THF. The reaction mixture was stirred at 23° C. for 18 hours. 1.0 mL 6N hydrochloric acid was added and the mixture was heated under reflux for 15 minutes. The solution was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic phase was dried (magnesium sulfate) and concentrated under reduced pressure. 3-Fluoro-N-(5-methylaminomethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzenesulfonamide was isolated as the crystalline oxalate salt, 0.05 grams (24%), m.p. 135-136° C., M+H=349.
Aufarbeitung
- temperaturethe mixture was heated
- temperatureunder reflux for 15 minutes
- concentrationThe solution was concentrated under reduced pressure
- customthe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
- dry with materialThe organic phase was dried (magnesium sulfate)
- concentrationconcentrated under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-b7032a57914543d583a85c6c3002fca5
- Quelldatensatz
- uspto-grants-2009_05
- Patentnummer
- US07531577B2
Notizen zur Reaktion
Wird geladen…