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

HRID 349032

反応式

HRID 349032 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-c934f471d600448b8101357bed9f443d
出典データセット
uspto-grants-2007_02
特許番号
US07176242B2

関連ノート

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