1,8-Diazabicyclo(5.4.0)undec-7-ene → (R)-3-(1-azidoethyl)-5-(prop-1-en-2-yl)pyridine

HRID 2071025노트

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HRID 2071025 반응식
C1C=CC(P([N:15]=[N+:16]=[N-:17])(C2C=CC=CC=2)=O)=CC=1.[CH2:18]=[C:19]([C:21]1[CH:22]=[C:23]([C@@H:27](O)[CH3:28])[CH:24]=[N:25][CH:26]=1)[CH3:20].C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1.CCOC(C)=O>[N:15]([C@@H:27]([C:23]1[CH:24]=[N:25][CH:26]=[C:21]([C:19]([CH3:20])=[CH2:18])[CH:22]=1)[CH3:28])=[N+:16]=[N-:17]

참가 물질

6

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 68671685(S)-1-(5-(prop-1-en-2-yl)pyridin-3-yl)ethanol

생성물 1

HCID 86647423(R)-3-(1-azidoethyl)-5-(prop-1-en-2-yl)pyridine수율 84.8%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

DPPA (0.55 mL, 2.55 mmol) was added to (S)-1-(5-(prop-1-en-2-yl)pyridin-3-yl)ethanol (347 mg, 2.13 mmol) in toluene (5 mL) and the reaction is cooled to 0° C. DBU (0.38 mL, 2.55 mmol) was added, the reaction was allowed to warm to room temperature and stirred overnight, diluted with EtOAc and washed with water. The organic layer was dried with Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (35% EtOAc in hexanes) to provide 340 mg of (R)-3-(1-azidoethyl)-5-(prop-1-en-2-yl)pyridine.

후처리

  1. temperatureto warm to room temperature
  2. washwashed with water
  3. dry with materialThe organic layer was dried with Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (35% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-35d16d4413484ef493ba4ac616220bad
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299267B2

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