반응 #2268867

반응 방정식

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

NaHCO3

→

yellow foam

수율 92.2%

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

수율 92.2%

용매

MeOH

반응 조건

후처리

1. 1
   기타The volatiles are removed in vacuo
2. 2
   기타the residue is chromatographed over 30 g silica gel (230-400 mesh)
3. 3
   세척eluting with 8% MeOH/CHCl3+1% conc. NH4OH
4. 4
   농축concentrated

실험 절차

N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-3-[(trimethylsilyl)ethynyl]-1-benzofuran-5-carboxamide (255 mg, 0.70 mmol) is dissolved in MeOH (6 ml). The solution is treated with saturated NaHCO3 (2 ml) and the reaction is stirred overnight at RT. The volatiles are removed in vacuo and the residue is chromatographed over 30 g silica gel (230-400 mesh) eluting with 8% MeOH/CHCl3+1% conc. NH4OH. The appropriate fractions are combined and concentrated to give 190 mg of a yellow foam. The foam is crystallized from Et2O to provide 138 mg (67%) of Example 22 as a pale yellow solid. HRMS (ESI) calcd for C18H18N2O2+H: 295.1446, found 295.1458 (M+H)+.

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