反応 #51177

反応方程式

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

2-aminopyridine

AcOH

→

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

溶媒

trimethylorthoformate

反応条件

後処理

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

実験手順

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.

出典