반응 #43736

반응 방정식

sodium hydroxide

water

tin(II) chloride

N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-5-nitro-1-benzofuran-2-carboxamide

→

title compound

N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-amino-1-benzofuran-2-carboxamide

용매

DMF

반응 조건

후처리

1. 1
   추출The aqueous phase is extracted six times with ethyl acetate
2. 2
   건조The combined organic phases are dried over magnesium sulfate
3. 3
   기타the solvent is removed under reduced pressure
4. 4
   기타a rotary evaporator
5. 5
   workup.STIRRINGshaken together with acidic ion exchange resin (Dowex WX2-200) for about 20 min
6. 6
   세척The loaded ion exchanger is washed three times with in each ase 30 ml of methanol
7. 7
   세척The product is eluted
8. 8
   기타The solvent is removed under reduced pressure
9. 9
   기타a rotary evaporator

실험 절차

2.0 ml (4 mmol) of a 2 M tin(II) chloride solution in DMF are added to N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-5-nitro-1-benzofuran-2-carboxamide (100 mg, 0.32 mmol). The mixture is stirred overnight. The reaction mixture is poured into water and made basic using 1N aqueous sodium hydroxide solution. The aqueous phase is extracted six times with ethyl acetate. The combined organic phases are dried over magnesium sulfate, and the solvent is removed under reduced pressure using a rotary evaporator. The crude product is taken up in methanol and shaken together with acidic ion exchange resin (Dowex WX2-200) for about 20 min. The loaded ion exchanger is washed three times with in each ase 30 ml of methanol, then with water/methanol 8:2, again with methanol, with dichloromethane and finally again with methanol. The product is eluted using methanol/triethylamine 95:5. The solvent is removed under reduced pressure using a rotary evaporator. 52 mg (58% of theory) of the title compound are isolated.

출처