反応 #44601

反応方程式

di-tert-butylcarbonate

triphenylphosphine

THF

(1R,2S)-1-azido-1-(3,4,5-trifluorophenyl)propan-2-ol

→

title compound

収率 86.3%

[(1R,2S)-2-hydroxy-1-(3,4,5-trifluorophenyl)propyl]carbamic acid tert-butyl ester

収率 86.3%

溶媒

water

反応条件

後処理

1. 1
   workup.STIRRINGThis mixture was stirred at 60° C. for 3.5 hr
2. 2
   温度The reaction solution was cooled to room temperature
3. 3
   その他The resulting reaction solution
4. 4
   workup.STIRRINGwas stirred at room temperature for 45 min
5. 5
   濃縮concentrated under reduced pressure
6. 6
   その他The obtained residue was purified by silica gel column chromatography (toluene:ethyl acetate=9:1)

実験手順

In nitrogen atmosphere, triphenylphosphine (5.85 g) was added to a THF solution (75 mL) of (1R,2S)-1-azido-1-(3,4,5-trifluorophenyl)propan-2-ol (5.16 g). This reaction solution was stirred at room temperature for 10 min, then water (5 mL) was added the reaction solution. This mixture was stirred at 60° C. for 3.5 hr. The reaction solution was cooled to room temperature, and then di-tert-butylcarbonate (5.35 g) was added to the reaction solution. The resulting reaction solution was stirred at room temperature for 45 min and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (toluene:ethyl acetate=9:1) to give 5.88 g of the title compound. The physical property values of this compound were as follows:

出典