Water → Tert-butyl 4-(4-(ethoxycarbonyl)-1H-pyrazol-1-YL)piperidine-1-carboxylate

HRID 1427009

반응식

HRID 1427009 반응식
CS(O[CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)(=O)=O.[NH:19]1[CH:23]=[C:22]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:21]=[N:20]1.[H-].[Na+].O>CN(C)C=O.C(OCC)(=O)C>[CH2:27]([O:26][C:24]([C:22]1[CH:23]=[N:19][N:20]([CH:6]2[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]2)[CH:21]=1)=[O:25])[CH3:28]

참가 물질

7

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

생성물 1

HCID 45926154Tert-butyl 4-(4-(ethoxycarbonyl)-1H-pyrazol-1-YL)piperidine-1-carboxylate수율 68%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

tert-Butyl 4-((methylsulfonyl)oxy)piperidine-1-carboxylate described in Production Example 13-1 (2.7 g, 9.67 mmol) and commercially available ethyl 4-pyrazole carboxylate (1.49 g, 10.6 mmol) were dissolved in N,N-dimethylformamide (30 mL), 50-72% oily sodium hydride (570 mg) was added at 0° C., and the mixture was heated and stirred at 60° C. for 11 hours. The reaction mixture was cooled to room temperature and water and ethyl acetate were added for partition. The organic layer was washed with water twice and then dried over anhydrous sodium sulfate and filtered. The solvent was evaporated, the resultant residue was dissolved in dichloromethane, the resultant was purified with silica gel column chromatography (n-heptane:ethyl acetate=4:1-1:1-1:3-0:1), and the target fraction was concentrated under vacuum to obtain the title compound (2.11 g, 68%).

후처리

  1. temperaturethe mixture was heated
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customfor partition
  4. washThe organic layer was washed with water twice
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was evaporated
  8. dissolutionthe resultant residue was dissolved in dichloromethane
  9. customthe resultant was purified with silica gel column chromatography (n-heptane:ethyl acetate=4:1-1:1-1:3-0:1)
  10. concentrationthe target fraction was concentrated under vacuum

출처 및 근거

ORD 기록
ord-c7b0bc050bf042c9b75d2fad693c7bb3
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933099B2

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