Реакция #640577

Уравнение реакции

water

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

triethylamine

triphosgene

→

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

Выход 89.9%

Растворители

toluene

toluene

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas slowly added dropwise
2. 2
   Температураheated
3. 3
   Температураto reflux for six hours
4. 4
   Температураto cool
5. 5
   Экстракцияextracted with ethyl acetate
6. 6
   ПромывкаThe organic layer was washed with 0.1 N hydrochloric acid water
7. 7
   Сушкаdried over anhydrous sodium sulfate
8. 8
   Другоеthe solvent was evaporated under reduced pressure
9. 9
   ДругоеThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Методика

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).

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