反応 #43751

反応方程式

N-[(3S)-1-azabicyclo[2.2.2]oct-3-yl]-5-nitro-1-benzo-thiophene-2-carboxamide hydrochloride

acetic acid

→

title compound

N-[(3S)-1-Azabicyclo[2.2.2]oct-3-yl]-5-amino-1-benzothiophene-2-carboxamide dihydrochloride

溶媒

water

反応条件

後処理

1. 1
   ろ過The reaction mixture is filtered through kieselguhr
2. 2
   洗浄the filter cake is washed with methanol
3. 3
   濃縮The filtrate is concentrated under reduced pressure
4. 4
   その他the residue is purified by preparative HPLC
5. 5
   workup.DISSOLUTIONThe product fraction is dissolved in 4M of HCl in dioxane
6. 6
   濃縮concentrated under reduced pressure
7. 7
   その他recrystallized from acetonitrile

実験手順

422 mg (1.15 mmol) of N-[(3S)-1-azabicyclo[2.2.2]oct-3-yl]-5-nitro-1-benzo-thiophene-2-carboxamide hydrochloride are suspended in 10 ml of a 1:1 mixture of acetic acid and water. 300.0 mg (4.59 mmol) of zinc are added, the mixture is then stirred at RT for 1 h. The reaction mixture is filtered through kieselguhr, and the filter cake is washed with methanol. The filtrate is concentrated under reduced pressure and the residue is purified by preparative HPLC. The product fraction is dissolved in 4M of HCl in dioxane, concentrated under reduced pressure and recrystallized from acetonitrile. 203 mg (47.3% of theory) of the title compound are obtained. The analytical data correspond to those of the enantiomeric compound from example 62.

出典