反应 #52177

反应方程式

diethyl (S)-2-(4-aminophthalimido)glutarate

HCl

→

Diethyl (S)-2-(5-amino-1-oxo-2-isoindolinyl)glutarate

溶剂

ethanol

反应条件

后处理

1. 1
   其他has reached −40° C
2. 2
   过滤The excess of Zn was filtered from the solution, 10% palladium on carbon (1.0 g)
3. 3
   workup.ADDITIONwas added
4. 4
   workup.STIRRINGthe solution shaken under hydrogen at (30-50 psi) overnight
5. 5
   其他The catalyst was removed by filtration through celite
6. 6
   浓缩the filtrate concentrated in vacuo
7. 7
   其他The residue was absorbed onto silica gel (15 g)
8. 8
   其他purified by chromatography on silica gel (440 g)
9. 9
   洗涤eluting with ethyl acetate

实验过程

A solution of diethyl (S)-2-(4-aminophthalimido)glutarate (10.5 g, 30.2 mmol) in ethanol (150 ml) was cooled in an acetonitrile/CO2 bath. Concentrated HCl (25 ml) was added followed by 30 mesh granular Zn (10:5 g, 0.161 mole) (Fisher) when the internal temperature has reached −40° C. The reaction mixture was stirred 1.5 hours at this temperature and a further 1 hour at −10° C. The excess of Zn was filtered from the solution, 10% palladium on carbon (1.0 g) was added, and the solution shaken under hydrogen at (30-50 psi) overnight. The catalyst was removed by filtration through celite and the filtrate concentrated in vacuo. The residue was absorbed onto silica gel (15 g) and purified by chromatography on silica gel (440 g) eluting with ethyl acetate:methylene chloride (1:14 g).

来源