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Dimethylformamide → Tert-butyl 4-(5-bromopyrazin-2-yloxy)piperidine-1-carboxylate

HRID 1666551
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HRID 1666551 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C.[Br:12][C:13]1[CH:18]=[N:17][C:16]([OH:19])=[CH:15][N:14]=1.[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30](OS(C)(=O)=O)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21]>O>[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([O:19][C:16]2[CH:15]=[N:14][C:13]([Br:12])=[CH:18][N:17]=2)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 178516739HCID 178516739, 화합물

생성물 1

HCID 58456669Tert-butyl 4-(5-bromopyrazin-2-yloxy)piperidine-1-carboxylate수율 96.7%

시약·촉매·용매 1

HCID 962
Water
용매

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온도
90 °C

실험 절차

Cesium carbonate (372 mg) was added to a DMF solution (2 ml) of 2-bromo-5-hydroxypyrazine (100 mg) and 1-t-butoxycarbonyl-4-(methanesulfonyloxy)piperidine (192 mg), and stirred at 90° C. for 14 hours. The reaction mixture was cooled to room temperature, water was added thereto and extracted with ethyl acetate. The organic layer was washed with saturated saline solution, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (C-300, hexane:ethyl acetate=1:11) to obtain the entitled compound (198 mg).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated saline solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified through silica gel column chromatography (C-300, hexane:ethyl acetate=1:11)

출처 및 근거

ORD 기록
ord-33d126b29dd34a709777559deb4793ff
출처 데이터셋
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08044070B2

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