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Isobutyraldehyde → Ethyl [(1-isopropyl-4,4,7-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)isobutylamino]benzoate

HRID 365525
ノート
印刷プレビュー

反応式

HRID 365525 の反応式
[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([NH:15][C:16]3[CH:26]=[CH:25][CH:24]=[CH:23][C:17]=3[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:11]([CH3:14])[CH:12]=2)[C:7]([CH3:28])([CH3:27])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[CH:29](=O)[CH:30]([CH3:32])[CH3:31].C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C.C(#N)C>[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([N:15]([C:16]3[CH:26]=[CH:25][CH:24]=[CH:23][C:17]=3[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:29][CH:30]([CH3:32])[CH3:31])=[C:11]([CH3:14])[CH:12]=2)[C:7]([CH3:28])([CH3:27])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6561IsobutyraldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 86755923Ethyl [(1-isopropyl-4,4,7-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)amino)benzoate2 回

生成物 1

HCID 53918247Ethyl [(1-isopropyl-4,4,7-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)isobutylamino]benzoate収率 34.4%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6342Acetonitrile溶媒

実験手順

Ethyl [(1-isopropyl-4,4,7-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)amino)benzoate (Compound 20, 0.12 g, 0.32 mmol) was dissolved in a 10% acetic acid in acetonitrile solution (2.0 mL). The solution was treated with isobutyraldehyde (0.10 mL, 1.1 mmol) and then sodium cyanoborohydride (22 mg, 0.35 mmol) and the reaction stirred at room temperature for 7 hours. 1 M aqueous NaOH was added until pH=6 was reached and the solution was extracted with ether (2×), washed with brine, and dried (Na2SO4). The filtered solution was concentrated under reduced pressure and the residue purified using flash column chromatography (10% ethyl acetate in hexanes) to give the title compound (48 mg) as an oil.

後処理

  1. extractionthe solution was extracted with ether (2×)
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationThe filtered solution was concentrated under reduced pressure
  5. customthe residue purified

出典と根拠

ORDレコード
ord-6d6113f740af4727a3d9a05ec62a5eb6
出典データセット
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06127382

反応ノート

読み込み中…

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