반응 #45647

반응 방정식

ethyl acetate

triethylamine

(3S)-3-(dimethylamino)pyrrolidine

7-Fluoro-2-(1-hydroxy-1-methylethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

→

compound

수율 93.3%

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

수율 93.3%

용매

brine

dimethyl sulfoxide

반응 조건

후처리

1. 1
   온도cooled to room temperature
2. 2
   기타The aqueous layer was separated
3. 3
   추출this was extracted twice with ethyl acetate
4. 4
   세척this was washed with saturated brine
5. 5
   건조dried over anhydrous sodium sulfate
6. 6
   기타The insoluble matter was separated by filtration
7. 7
   기타the solvent was evaporated away
8. 8
   기타the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=9:1)

실험 절차

7-Fluoro-2-(1-hydroxy-1-methylethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-112) (35 mg, 0.11 mmol) was dissolved in anhydrous dimethyl sulfoxide (2 ml), and at room temperature, triethylamine (24 μl, 0.17 mmol) and (3S)-3-(dimethylamino)pyrrolidine (22 μl, 0.17 mmol) were added. This mixture liquid was stirred at 90° C. for 12 hours, then cooled to room temperature. This was fractionated with ethyl acetate and saturated brine. The aqueous layer was separated, and this was extracted twice with ethyl acetate. The organic layers were combined, this was washed with saturated brine, dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=9:1) to obtain the entitled compound (41.5 mg, 91%) as a white solid. This was further recrystallized from hexane/diethyl ether to obtain a cream powder (27.5 mg).

출처