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

HRID 365525
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HRID 365525 반응식
[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]
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반응물 4

HCID 6561IsobutyraldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 86755923Ethyl [(1-isopropyl-4,4,7-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)amino)benzoate2회

생성물 1

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

시약·촉매·용매

2
HCID 176Acetic Acid용매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6d6113f740af4727a3d9a05ec62a5eb6
출처 데이터셋
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06127382

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