Triethylamine → 1-(N-t-butoxycarbonyl-N-methylamino)-2-oxo-5-methylhexane
Reaktionsgleichung
[C:1]([O:5][C:6]([N:8]([CH2:10][CH:11]([OH:17])[CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C>CS(C)=O>[C:1]([O:5][C:6]([N:8]([CH2:10][C:11](=[O:17])[CH2:12][CH2:13][CH:14]([CH3:15])[CH3:16])[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of 1-(N-t-butoxycarbonyl-N-methylamino-2-hydroxy-5-methylhexane (2.45 g) and triethylamine (3.03 g) in dimethyl sulfoxide (20 ml) was added sulfur trioxide pyridine complex (4.77 g) under ice-bath cooling. After the mixture was stirred at ambient temperature overnight, the reaction mixture was poured into ice-water (100 ml). The mixture was extracted with diethyl ether (100 ml×2). The extract was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (20% ethyl acetate in n-hexane as eluent) to give 1-(N-t-butoxycarbonyl-N-methylamino)-2-oxo-5-methylhexane (2.15 g).