Sodium Hydroxide → Ethyl [(1-isopropyl-4,4,7-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)(cyclopropylmethyl)amino]benzoate

HRID 365523노트

반응식

HRID 365523 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].[CH2:29]1[CH:31]([CH:32](O)C#N)[CH2:30]1.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])[CH2:32][CH:31]3[CH2:29][CH2:30]3)=[C:11]([CH3:14])[CH:12]=2)[C:7]([CH3:28])([CH3:27])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 113893592-Cyclopropyl-2-hydroxyacetonitrileHCID 86755923Ethyl [(1-isopropyl-4,4,7-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)amino)benzoate2회

생성물 1

HCID 53850501Ethyl [(1-isopropyl-4,4,7-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)(cyclopropylmethyl)amino]benzoate수율 49%

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, 0.18 g, 0.47 mmol) was dissolved in a 10% acetic acid in acetonitrile solution (6.0 mL). The solution was treated with cyclopropylcarboxaldehyde (0.10 mL, 1.3 mmol) and then sodium cyanoborohydride (35 mg, 0.55 mmol) and the reaction was stirred at room temperature for 7 hours. 1M 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 compounds (0.1 g) 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-31a4a6e8a241485b84f6074345a678e7
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06127382

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