Triethylamine → 1-(3-Tert-butyldimethylsiloxy-3-cyclohexylpropyl)-4-(5-methylpyridin-2-yl)aminopiperidine

HRID 1820302노트

반응식

HRID 1820302 반응식
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH:9]1([CH:15]([OH:32])[CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][CH:21]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][N:26]=3)[CH2:20][CH2:19]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[O:32]([CH:15]([CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)[CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][CH:21]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][N:26]=2)[CH2:22][CH2:23]1)[Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 8471Triethylamine2회HCID 28928tert-Butyldimethylsilyl chloride2회HCID 231099131-(3-Cyclohexyl-3-hydroxypropyl)-4-(5-methylpyridin-2-yl)aminopiperidine

생성물 1

HCID 231099081-(3-Tert-butyldimethylsiloxy-3-cyclohexylpropyl)-4-(5-methylpyridin-2-yl)aminopiperidine수율 77.8%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매2회HCID 6344Dichloromethane용매

실험 절차

After adding tert-butyldimethylsilyl chloride (203 mg, 1.5 mmol) to a solution of 1-(3-cyclohexyl-3-hydroxypropyl)-4-(5-methylpyridin-2-yl)aminopiperidine (405 mg, 1.22 mmol), triethylamine (0.20 mL) and 4-dimethylaminopyridine (30 mg, 0.24 mmol) in methylene chloride (5 mL) while cooling on ice, the mixture was stirred at room temperature for 18 hours. Triethylamine (0.20 mL), 4-dimethylaminopyridine (30 mg, 1.5 mmol) and tert-butyldimethylsilyl chloride (203 mg, 1.5 mmol) were further added to the reaction mixture and stirring was continued at room temperature for 70 hours. NH silica Chromatorex DM1020 was added to the reaction mixture, which was then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (60 g NH silica Chromatorex DM2035, hexane:ethyl acetate=4:1) to obtain the title compound as a colorless oil (423 mg) (77.7% yield).

후처리

  1. temperaturewhile cooling on ice
  2. stirringstirring
  3. waitwas continued at room temperature for 70 hours
  4. additionNH silica Chromatorex DM1020 was added to the reaction mixture, which
  5. concentrationwas then concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (60 g NH silica Chromatorex DM2035, hexane:ethyl acetate=4:1)

출처 및 근거

ORD 기록
ord-d7d77854b8c8499a91141883bbe65d6f
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07601843B2

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