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Pyrrolidine → Methyl 2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-(pyrrolidin-1-yl)benzoate

HRID 1787890
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HRID 1787890 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:24]=[C:23](F)[CH:22]=[CH:21][C:16]=2[C:17]([O:19][CH3:20])=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:24]=[C:23]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[CH:22]=[CH:21][C:16]=2[C:17]([O:19][CH3:20])=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
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참가 물질

3

반응물 2

HCID 31268PyrrolidineHCID 57602502Methyl 2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-fluorobenzoate

생성물 1

HCID 57602510Methyl 2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-(pyrrolidin-1-yl)benzoate수율 282.8%

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온도
80 °C

실험 절차

The methyl 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-fluorobenzoate (7.99 mmol, 22.6 mmol) was diluted with pyrrolidine (18 mL, 215.6 mmol). The resulting mixture was heated to 80° C. After 3 h, the reaction mixture was cooled to room temperature and quenched with water (50 mL). The mixture was extracted with dichloromethane (200 mL). The organic layer was washed with saturated aqueous citric acid (3×50 mL), dried over sodium sulfate, filtered, and concentrated to give the title compound (9.14 g, 100%) as a colorless oil.

후처리

  1. temperaturethe reaction mixture was cooled to room temperature
  2. customquenched with water (50 mL)
  3. extractionThe mixture was extracted with dichloromethane (200 mL)
  4. washThe organic layer was washed with saturated aqueous citric acid (3×50 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-474ff65ba61c420db473efdf7d92bd68
출처 데이터셋
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07511066B2

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