Sodium Azide → (S)-2-azido-2-(6-methoxypyridin-3-yl)ethanol
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:11][O:10]2)=[CH:5][N:4]=1.[N-:12]=[N+:13]=[N-:14].[Na+].Cl([O-])(=O)(=O)=O.[Li+]>C(#N)C>[N:12]([C@@H:9]([C:6]1[CH:5]=[N:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[CH2:11][OH:10])=[N+:13]=[N-:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a stirred solution of (R)-2-methoxy-5-(oxiran-2-yl)pyridine (1.02 g, 6.75 mmol) in acetonitrile (100 mL) were added sodium azide (1.8 g, 27 mmol) and lithium perchlorate (11 g, 0.10 mol) and the mixture was stirred at 60° C. for 4 h. TLC indicated completion of the reaction. After cooling, the mixture was filtered through Celite and the filtrate was concentrated. The residue was treated with water and extracted with EtOAc (3×50 mL). The combined organic layers were washed with aq. NaHCO3 and brine, dried (Na2SO4), and concentrated. The residue was purified by silica gel column (0-50% EtOAc/hexane) to give a light yellow oil (0.9 g, 69%).
Workup
- customcompletion of the reaction
- temperatureAfter cooling
- filtrationthe mixture was filtered through Celite
- concentrationthe filtrate was concentrated
- additionThe residue was treated with water
- extractionextracted with EtOAc (3×50 mL)
- washThe combined organic layers were washed with aq. NaHCO3 and brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customThe residue was purified by silica gel column (0-50% EtOAc/hexane)
Sources & evidence
- ORD record
- ord-0711f347197f4e8f819d039ddab816d3
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653091B2
Reaction notes
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