反応 #60383

反応方程式

HCl

trifluoro-methanesulfonic acid 5-azido-5,6,7,8-tetrahydro-naphthalen-2-yl ester

trifluoro-methanesulfonic acid 5-azido-5,6,7,8-tetrahydro-naphthalen-2-yl Ester

PPh3

H2O

→

title compound

trifluoro-methanesulfonic acid 5-amino-5,6,7,8-tetrahydro-naphthalen-2-yl Ester

溶媒

THF

反応条件

後処理

1. 1
   抽出The mixture was extracted with toluene (3×100 mL)
2. 2
   抽出extracted with ether (3×150 mL)
3. 3
   乾燥The ether solution was dried over Na2SO4
4. 4
   ろ過filtered
5. 5
   濃縮concentrated in vacuo
6. 6
   その他The crude was purified by flash chromatography (6% MeOH—CH2Cl2)

実験手順

A solution of trifluoro-methanesulfonic acid 5-azido-5,6,7,8-tetrahydro-naphthalen-2-yl ester (Step C, 10.3 g, 32.1 mmol, 1.0 eq) in THF (70 mL) was added PPh3 (Aldrich, 8.4 g, 32.1 mmol, 1.0 eq), and H2O (30 mL) at 0° C. The mixture was warmed to RT and stirred overnight. 2 N HCl was added until the mixture was acidic (pH ˜1-2). The mixture was extracted with toluene (3×100 mL). The aqueous phase was neutralized with 5 N NaOH to pH around 12-13, and extracted with ether (3×150 mL). The ether solution was dried over Na2SO4 filtered and concentrated in vacuo. The crude was purified by flash chromatography (6% MeOH—CH2Cl2) to provide the title compound.

出典