1-Methylpyrrolidine → Prop-1-en-2-yl 5-(trifluoromethyl)pyridin-3-ylcarbamate

HRID 217871

반응식

HRID 217871 반응식
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([NH2:9])[CH:6]=[N:7][CH:8]=1.CN1CCCC1.Cl[C:19]([O:21][C:22]([CH3:24])=[CH2:23])=[O:20].CCOC(C)=O>C1COCC1.C(Cl)Cl.O>[F:11][C:2]([F:1])([F:10])[C:3]1[CH:4]=[C:5]([NH:9][C:19](=[O:20])[O:21][C:22]([CH3:24])=[CH2:23])[CH:6]=[N:7][CH:8]=1

참가 물질

8

반응물 4

HCID 84541-MethylpyrrolidineHCID 8857Ethyl AcetateHCID 93846Isopropenyl chloroformateHCID 140519365-(Trifluoromethyl)pyridin-3-amine

생성물 1

HCID 59588859Prop-1-en-2-yl 5-(trifluoromethyl)pyridin-3-ylcarbamate

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

5-(trifluoromethyl)pyridin-3-amine (883 mg, 5.45 mmol) was suspended in dry THF (20 mL) and N-methylpyrrolidine (680 μL, 6.54 mmol) was added to give a brown suspension. The mixture was cooled to 0° C. and isopropenyl chloroformate (715 μL, 6.54 mmol) was added dropwise over 15 min. The suspension was allowed to reach RT and was stirred for 4 h. EtOAc (60 mL) and H2O (10 mL) were added and the organic layer was isolated, washed with 50% brine (10 mL), dried (MgSO4), filtered and evaporated to leave a brown oil, which solidified upon standing (1.05 g). The solid was taken up in CH2Cl2 (4 mL) and purified by column chromatography on silica gel, eluting with EtOAc in CH2Cl2 (6%→40%), to give a white solid. Yield: 600 mg (45%).

후처리

  1. customto give a brown suspension
  2. customto reach RT
  3. customthe organic layer was isolated
  4. washwashed with 50% brine (10 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto leave a brown oil, which
  9. custompurified by column chromatography on silica gel
  10. washeluting with EtOAc in CH2Cl2 (6%→40%)
  11. customto give a white solid

출처 및 근거

ORD 기록
ord-1b800b78c88f466f99b47524793074aa
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198279B2

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