Butyl bromide → Methyl 1-butyl-1,2,3,4-tetrahydroquinoline-7-carboxylate

HRID 14242

반응식

HRID 14242 반응식
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C(=O)(O)[O-].[Cs+].[CH2:20](Br)[CH2:21][CH2:22][CH3:23]>C1COCC1.CCOC(C)=O>[CH2:20]([N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=2)[CH2:4][CH2:3][CH2:2]1)[CH2:21][CH2:22][CH3:23]

참가 물질

6

반응물 3

HCID 8002Butyl bromideHCID 2734983Cesium bicarbonateHCID 16244389Methyl 1,2,3,4-tetrahydroquinoline-7-carboxylate

생성물 1

HCID 21086131Methyl 1-butyl-1,2,3,4-tetrahydroquinoline-7-carboxylate수율 67.1%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of methyl 1,2,3,4-tetrahydroquinoline-7-carboxylate (180 mg, 0.94 mmol) and cesium bicarbonate (1.5 g, 4.7 mmol) in THF (2 mL) was added n-butyl bromide (1.0 mL, 9.4 mmol), and the reaction mixture was heated at reflux for 48 h. The reaction mixture was cooled to room temperature, and diluted with EtOAc. The organic layer was washed with water, and brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:3 ethyl acetate/hexanes) afforded methyl 1-butyl-1,2,3,4-tetrahydroquinoline-7-carboxylate (156 mg): ESI MS m/z 248 [M+H]+.

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 48 h
  3. washThe organic layer was washed with water, and brine
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash column chromatography (silica, 1:3 ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-3aaa66ee44c24706a33c8f1585534b8e
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727997B2

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