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

HRID 2071025ノート

反応式

HRID 2071025 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-35d16d4413484ef493ba4ac616220bad
出典データセット
uspto-grants-2012_10
特許番号
US08299267B2

反応ノート

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