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

HRID 2071025Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2071025
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]

Komponenten

6

Edukt 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

Produkt 1

HCID 86647423(R)-3-(1-azidoethyl)-5-(prop-1-en-2-yl)pyridineAusbeute 84,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-35d16d4413484ef493ba4ac616220bad
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299267B2

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