반응 #45787

반응 방정식

Ethyl (1R*,2R*)-2-[4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-yl]cyclopropanecarboxylate

triethylamine

(3S)-3-(dimethylamino)pyrrolidine

→

compound

수율 42.0%

Ethyl (1R*,2R*)-2-{4-cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}cyclopropanecarboxylate

수율 42.0%

용매

dimethyl sulfoxide

반응 조건

후처리

1. 1
   온도After cooled
2. 2
   농축this was concentrated under reduced pressure
3. 3
   workup.ADDITIONdiluted with chloroform
4. 4
   세척washed with saturated brine
5. 5
   건조The organic layer was dried over anhydrous magnesium sulfate
6. 6
   기타the solvent was evaporated away under reduced pressure

실험 절차

Ethyl (1R*,2R*)-2-[4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-yl]cyclopropanecarboxylate (I-216) (200 mg, 0.55 mmol) was dissolved in dimethyl sulfoxide (5 ml), then triethylamine (146 μl, 1.10 mmol) and (3S)-3-(dimethylamino)pyrrolidine (146 μl, 1.15 mmol) were added, followed by stirring at 95° C. for 4 hours. After cooled, this was concentrated under reduced pressure, diluted with chloroform, and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated away under reduced pressure. The resulting residue was subjected to preparative TLC. The eluate with chloroform/methanol (5:1, v/v) gave the entitled compound (105 mg, 42%) as a red brown solid.

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