반응 #43739

반응 방정식

tin(II) chloride

N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-nitro-1-benzofuran-2-carboxamide

→

title compound

N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-6-amino-1-benzofuran-2-carboxamide

용매

DMF

반응 조건

후처리

1. 1
   기타The solvent is removed under reduced pressure
2. 2
   기타a rotary evaporator
3. 3
   workup.STIRRINGshaken for about 1 h
4. 4
   세척The loaded ion exchanger is washed with methanol
5. 5
   세척The product is eluted with methanol/triethylamine 95:5
6. 6
   기타The solvent is removed under reduced pressure
7. 7
   기타a rotary evaporator
8. 8
   기타The crude product is purified on silica gel 60 (mobile phase: dichloromethane/triethylamine 100:1→dichloro-methane/methanol/triethylamine 100:1:1→dichloromethane/methanol/triethylamine 90:10:1)

실험 절차

15.0 ml (30 mmol) of a 2 M tin(II) chloride solution in DMF are added to N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-nitro-1-benzofuran-2-carboxamide (1550 mg, 4.92 mmol). The mixture is stirred overnight. The solvent is removed under reduced pressure using a rotary evaporator. The crude product is taken up in methanol and, together with acidic ion exchange resin (Dowex WX2-200), shaken for about 1 h. The loaded ion exchanger is washed with methanol, then with water, DMF, again with methanol, with dichloromethane and finally again with methanol. The product is eluted with methanol/triethylamine 95:5. The solvent is removed under reduced pressure using a rotary evaporator. The crude product is purified on silica gel 60 (mobile phase: dichloromethane/triethylamine 100:1→dichloro-methane/methanol/triethylamine 100:1:1→dichloromethane/methanol/triethylamine 90:10:1). 643 mg (46% of theory) of the title compound are isolated.

출처