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

HRID 2071025Notes

Reaction equation

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]

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-35d16d4413484ef493ba4ac616220bad
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299267B2

Reaction notes

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