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

HRID 217871ノート

反応式

HRID 217871 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-1b800b78c88f466f99b47524793074aa
出典データセット
uspto-grants-2012_06
特許番号
US08198279B2

反応ノート

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