반응 #45725

반응 방정식

ethyl acetate

triethylamine

(3S)-3-(dimethylamino)pyrrolidine

2-Cyclopropyl-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

→

product

수율 69.0%

2-Cyclopropyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

수율 69.0%

용매

brine

dimethyl sulfoxide

반응 조건

후처리

1. 1
   기타the reaction liquid
2. 2
   추출The aqueous layer was further extracted twice with ethyl acetate
3. 3
   세척washed with saturated brine
4. 4
   건조dried over anhydrous sodium sulfate
5. 5
   기타The insoluble matter was separated by filtration
6. 6
   기타the solvent was evaporated away
7. 7
   기타the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=97:3)

실험 절차

2-Cyclopropyl-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-173) (70 mg, 0.24 mmol) was dissolved in dimethyl sulfoxide (2 ml), then at room temperature, triethylamine (50 μl, 0.36 mmol) and (3S)-3-(dimethylamino)pyrrolidine (40 μl, 0.31 mmol) were added. After cooling to room temperature, the reaction liquid was fractionated with ethyl acetate and saturated brine. The aqueous layer was further extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, then the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=97:3) to obtain a roughly-purified product (64 mg, 69%).

출처