Reaktion #640577

Reaktionsgleichung

water

2-Methyl-4-(2-nitrobenzylamino)butanol

triethylamine

triphosgene

→

6-methyl-3-(2-nitrobenzyl)-[1,3]-oxazepan-2-one

Ausbeute 89.9%

Lösungsmittel

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas slowly added dropwise
2. 2
   Temperaturheated
3. 3
   Temperaturto reflux for six hours
4. 4
   Temperaturto cool
5. 5
   Extraktionextracted with ethyl acetate
6. 6
   WaschenThe organic layer was washed with 0.1 N hydrochloric acid water
7. 7
   Trocknendried over anhydrous sodium sulfate
8. 8
   Sonstigethe solvent was evaporated under reduced pressure
9. 9
   SonstigeThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Vorschrift

2-Methyl-4-(2-nitrobenzylamino)butanol (5.00 g, 21.0 mmol), triethylamine (8.49 g, 84.1 mmol) were dissolved in toluene (50 ml). Under ice cooled condition, a solution in which triphosgene (2.50 g, 8.42 mmol) was dissolved in toluene (10 ml) was slowly added dropwise thereto and heated to reflux for six hours after stirred at room temperature for one hour. The reaction mixture was poured into water and, after standing to cool, extracted with ethyl acetate. The organic layer was washed with 0.1 N hydrochloric acid water and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain 6-methyl-3-(2-nitrobenzyl)-[1,3]-oxazepan-2-one (2.00 g).

Quelle