Borane;tetrahydrofuran → 4-Aminomethyl-1-(1-naphthylsulfonyl)piperidine
Reaktionsgleichung
[NH2:1][C:2]([CH:4]1[CH2:9][CH2:8][N:7]([S:10]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH2:6][CH2:5]1)=O.B.O1CCCC1>O1CCCC1>[NH2:1][CH2:2][CH:4]1[CH2:9][CH2:8][N:7]([S:10]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH2:6][CH2:5]1Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
To a solution of 4-aminocarbonyl-1-(1-naphthylsulfonyl)piperidine (10.6 g, 33.3 mmol) in tetrahydrofuran (200 mL) stirring under argon at room temperature, was added borane-tetrahydrofuran complex (1.5 M in tetrahydrofuran, 67 mL, 100 mmol). The resulting solution was heated to 80° C. for 6 h before the solvent was evaporated under vacuum. The residue was dissolved in 1.0 M aqueous hydrochloric acid (100 mL), and this was washed with diethyl ether (100 mL twice). The aqueous layer was basified to pH 10 with 50% aqueous sodium hydroxide and extracted with dichloromethane (50 mL three times). The combined dichloromethane extracts were dried (anhydrous sodium sulfate) and evaporated under vacuum to obtain 4-aminomethyl-1-(1-naphthylsulfonyl)piperidine (9.1 g, 90% yield).
Aufarbeitung
- customwas evaporated under vacuum
- dissolutionThe residue was dissolved in 1.0 M aqueous hydrochloric acid (100 mL)
- washthis was washed with diethyl ether (100 mL twice)
- extractionextracted with dichloromethane (50 mL three times)
- dry with materialThe combined dichloromethane extracts were dried (anhydrous sodium sulfate)
- customevaporated under vacuum
Quellen und Nachweise
- ORD-Eintrag
- ord-96211a1ab580490d902bc8dbc4f521a4
- Quelldatensatz
- uspto-grants-2009_04
- Patentnummer
- US07517991B2
Notizen zur Reaktion
Wird geladen…