Reaction #640571

Reaction equation

water

triethylamine

triphosgene

3-(2-Nitrobenzylamino)-1-propanol

→

3-(2-nitrobenzyl)-[1,3]-oxazinan-2-one

Yield 63.0%

Solvents

chloroform

Conditions

Workup

1. 1
   Extractionextracted with ethyl acetate
2. 2
   Washafter the organic layer was washed with a saturated brine, it
3. 3
   Dryingwas dried over anhydrous sodium sulfate
4. 4
   Otherthe solvent was evaporated under reduced pressure
5. 5
   OtherThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:4)

Procedure

3-(2-Nitrobenzylamino)-1-propanol (1.03 g, 4.90 mmol) was dissolved in chloroform (20 ml) and the reaction solution was cooled to 0° C. Then triethylamine (1.98 g, 19.6 mmol), triphosgene (0.58 g, 1.95 mmol) were added thereto and the mixture was stirred at the same temperature for 1.5 hours. The reaction mixture was added with water and extracted with ethyl acetate and after the organic layer was washed with a saturated brine, it was 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=1:4) and 3-(2-nitrobenzyl)-[1,3]-oxazinan-2-one (0.29 g) was obtained.

Source