Triphenylphosphine → (S)-2-Chloro-4-(1-amino)ethylpyridine
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([C@H:23]([C:25]1[CH:30]=[CH:29][N:28]=[C:27]([Cl:31])[CH:26]=1)[CH3:24])=[N+]=[N-]>O1CCCC1.O>[Cl:31][C:27]1[CH:26]=[C:25]([C@@H:23]([NH2:20])[CH3:24])[CH:30]=[CH:29][N:28]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
Triphenylphosphine (9.56 g) was added to a solution of 4-((S)-1-azidoethyl)-2-chloropyridine (4.44 g) in tetrahydrofuran-water (4:1, 50 mL), and the reaction solution was heated and stirred at 60° C. for two hours. The reaction solution was returned to room temperature, and the solvent was evaporated under reduced pressure. Chloroform and 5 N hydrochloric acid were added to the residue, and the aqueous layer was separated. The aqueous layer was made basic with 5 N sodium hydroxide. Chloroform was added to the reaction solution, and the organic layer was separated. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain the title compound (2.24 g). The property values of the compound are as follows.
Workup
- temperaturethe reaction solution was heated
- customwas returned to room temperature
- customthe solvent was evaporated under reduced pressure
- additionChloroform and 5 N hydrochloric acid were added to the residue
- customthe aqueous layer was separated
- additionChloroform was added to the reaction solution
- customthe organic layer was separated
- dry with materialThe organic layer was dried over magnesium sulfate
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-b387d1ad6ea247238838b69b09908834
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07618960B2
Reaction notes
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