반응 #51177

반응 방정식

methyl (3-formylphenyl)-5-oxopyrrolidine-3-carboxylate

2-aminopyridine

AcOH

→

methyl 5-oxo-1-{3-((2-pyridylamino)methyl)phenyl}pyrrolidine-3-carboxylate

용매

trimethylorthoformate

반응 조건

후처리

1. 1
   농축The reaction mixture was concentrated in vacuo
2. 2
   workup.DISSOLUTIONthe residue was re-dissolved in methanol
3. 3
   workup.ADDITIONAcOH was added
4. 4
   농축The reaction solution was then concentrated in vacuo
5. 5
   workup.DISSOLUTIONThe residue was dissolved in EtOAc
6. 6
   세척organic solution was washed with saturated NaHCO3 twice
7. 7
   건조The organic layer was dried over Na2SO4
8. 8
   농축concentrated in vacuo
9. 9
   기타The crude product was purified by silica gel chromatograph (10% meOH/EtOAc)
10. 10
    기타to provide an orange oil

실험 절차

A solution of methyl (3-formylphenyl)-5-oxopyrrolidine-3-carboxylate, 2-aminopyridine, and AcOH in trimethylorthoformate was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and the residue was re-dissolved in methanol. The solution was then cooled to 0° C. AcOH was added followed by NaBH3CN solid in portions. The reaction was allowed to stirred at room temperature for 8 hours. The reaction solution was then concentrated in vacuo. The residue was dissolved in EtOAc and organic solution was washed with saturated NaHCO3 twice. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude product was purified by silica gel chromatograph (10% meOH/EtOAc) to provide an orange oil.

출처