반응 #45899

반응 방정식

trifluoroacetic acid

tert-Butyl (2S)-2-[(dimethylamino)methyl]pyrrolidine-1-carboxylate

triethylamine

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

→

compound

수율 20.0%

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

수율 20.0%

용매

dichloromethane

반응 조건

후처리

1. 1
   기타The reaction liquid
2. 2
   농축was concentrated under reduced pressure
3. 3
   workup.DISSOLUTIONthe residue was dissolved in dimethyl sulfoxide (2 ml)
4. 4
   workup.STIRRINGby stirring in an oil bath at 100° C. for 5 hours
5. 5
   기타The reaction liquid
6. 6
   농축was concentrated under reduced pressure
7. 7
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
8. 8
   세척washed with water and saturated brine
9. 9
   건조After drying over anhydrous sodium sulfate
10. 10
    기타the insoluble matter was separated by filtration
11. 11
    기타the residue obtained by concentration
12. 12
    기타was purified by preparative TLC (eluent, chloroform

실험 절차

tert-Butyl (2S)-2-[(dimethylamino)methyl]pyrrolidine-1-carboxylate (I-328) (92.0 mg, 0.403 mmol) was dissolved in dichloromethane (1 ml), and at room temperature, trifluoroacetic acid (1 ml) was added, followed by stirring at room temperature for 1 hour. The reaction liquid was concentrated under reduced pressure, the residue was dissolved in dimethyl sulfoxide (2 ml), then triethylamine (84.2 μl, 0.604 mmol) and 2-cyclopropyl-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-173) (118 mg, 0.403 mmol) was added, followed by stirring in an oil bath at 100° C. for 5 hours. The reaction liquid was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, and washed with water and saturated brine. After drying over anhydrous sodium sulfate, the insoluble matter was separated by filtration, the residue obtained by concentration was purified by preparative TLC (eluent, chloroform:methanol=10:1, v/v) to obtain the entitled compound (32.0 mg, 20%) as a colorless oily substance.

출처