反应 #811404

反应方程式

ammonium chloride

5,6-dihydro-7H-pyrrolo[1,2-c]imidazol-7-one

n-butyl lithium hexane

6-bromo-N-methyl-2-naphthamide

→

title compound

收率 36.6%

6-(7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide

收率 36.6%

溶剂

THF

THF

THF

反应条件

后处理

1. 1
   workup.ADDITIONwas added to this solution at not more than −55° C.
2. 2
   workup.STIRRINGThe mixture was stirred at the same temperature for 1.5 h
3. 3
   其他the reaction
4. 4
   其他The solvent was evaporated under reduced pressure
5. 5
   萃取an ethanol-soluble material was extracted from the resulting residue
6. 6
   其他the solvent was evaporated again
7. 7
   其他The residue was purified by flash silica gel column chromatography (eluent, chloroform/methanol containing ammonia (7%), 19/1→9/1)
8. 8
   其他The eluate was recrystallized from methanol

实验过程

Dry THF (150 ml) was cooled to −65° C. in a dry ice-acetone bath under an argon atmosphere and n-butyl lithium hexane solution (1.6M: 45.2 ml) was added. A solution of 6-bromo-N-methyl-2-naphthamide (8.68 g) in dry THF (700 ml) cooled to 10° C. was added to this solution at not more than −55° C., and the mixture was stirred for 1 h. A dry THF solution (60 ml) of 5,6-dihydro-7H-pyrrolo[1,2-c]imidazol-7-one (3.65 g) was added dropwise. The mixture was stirred at the same temperature for 1.5 h and saturated aqueous ammonium chloride solution (120 ml) was added to stop the reaction. The solvent was evaporated under reduced pressure and an ethanol-soluble material was extracted from the resulting residue and the solvent was evaporated again. The residue was purified by flash silica gel column chromatography (eluent, chloroform/methanol containing ammonia (7%), 19/1→9/1). The eluate was recrystallized from methanol to give the title compound (3.36 g) as colorless crystals.

来源