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

HRID 349032

반응식

HRID 349032 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-c934f471d600448b8101357bed9f443d
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176242B2

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