反应 #51177

反应方程式

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

2-aminopyridine

AcOH

→

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

溶剂

trimethylorthoformate

反应条件

后处理

1. 1
   浓缩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
   浓缩The reaction solution was then concentrated in vacuo
5. 5
   workup.DISSOLUTIONThe residue was dissolved in EtOAc
6. 6
   洗涤organic solution was washed with saturated NaHCO3 twice
7. 7
   干燥The organic layer was dried over Na2SO4
8. 8
   浓缩concentrated in vacuo
9. 9
   其他The crude product was purified by silica gel chromatograph (10% meOH/EtOAc)
10. 10
    其他to provide an orange oil

实验过程

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.

来源