반응 #45629

반응 방정식

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

hydrochloric acid ethanol

hydrogen

→

compound

수율 16.1%

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

수율 16.1%

용매

ethanol

반응 조건

후처리

1. 1
   workup.ADDITION10% carbon-held palladium catalyst was added
2. 2
   여과After filtration through Celite
3. 3
   농축the solvent was concentrated under reduced pressure, ethyl acetate
4. 4
   workup.ADDITIONan aqueous saturated sodium hydrogencarbonate solution were added
5. 5
   세척The organic layer was washed with saturated brine
6. 6
   건조dried over anhydrous sodium sulfate
7. 7
   기타The solvent was evaporated away
8. 8
   세척eluted with a mixed solvent of chloroform/methanol (20:1
9. 9
   기타v/v), recrystallized
10. 10
    기타purified with n-hexane/ethyl acetate/diisopropyl ether

실험 절차

7-[(3S)-3-(Dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-2-[(E)-2-phenylethenyl]-1,3-benzoxazole-4-carbonitrile (I-93) (100 mg, 0.22 mmol) and 1 N hydrochloric acid/ethanol solution (223 μl, 10.22 mmol) were dissolved in ethanol (2 ml), 10% carbon-held palladium catalyst was added, followed by stirring at room temperature under atmospheric pressure of hydrogen for 3 hours. After filtration through Celite, the solvent was concentrated under reduced pressure, ethyl acetate and an aqueous saturated sodium hydrogencarbonate solution were added to make the aqueous layer basic, followed by fractionation. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was evaporated away, the resulting residue was subjected to preparative thin-layer silica gel column chromatography, eluted with a mixed solvent of chloroform/methanol (20:1, v/v), recrystallized and purified with n-hexane/ethyl acetate/diisopropyl ether to obtain the entitled compound (16 mg, 16%) as a white solid.

출처