Water → 4-((S)-1-azidoethyl)-2-chloropyridine
Reaction equation
C1(P([N:15]=[N+:16]=[N-:17])(C2C=CC=CC=2)=O)C=CC=CC=1.[Cl:18][C:19]1[CH:24]=[C:23]([C@H:25](O)[CH3:26])[CH:22]=[CH:21][N:20]=1.C1CCN2C(=NCCC2)CC1.O>C1(C)C=CC=CC=1.CCOCC>[N:15]([C@H:25]([C:23]1[CH:22]=[CH:21][N:20]=[C:19]([Cl:18])[CH:24]=1)[CH3:26])=[N+:16]=[N-:17]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Diphenylphosphoryl azide (6.57 mL) was added to a solution of (R)-1-(2-chloropyridin-4-yl)ethanol in toluene (50 mL) in a nitrogen atmosphere, and the reaction solution was cooled to 0° C. DBU (4.52 mL) was added to the reaction solution, which was then heated to room temperature and stirred overnight. Water and an ether were added to the reaction solution, and the organic layer was separated. The organic layer was dried over magnesium sulfate, and the residue was purified by silica gel chromatography (carrier: Chromatorex; elution solvent: hexane-ethyl acetate) to obtain the title compound (4.44 g) The property values of the compound are as follows.
Workup
- temperaturewas then heated to room temperature
- customthe organic layer was separated
- dry with materialThe organic layer was dried over magnesium sulfate
- customthe residue was purified by silica gel chromatography (carrier: Chromatorex; elution solvent: hexane-ethyl acetate)
Sources & evidence
- ORD record
- ord-76b223288c6a44d290805bd7b0c19f68
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07618960B2
Reaction notes
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