Sodium Azide → cis-2-Azidocyclopentyl 4-bromophenyl ether
Reaction equation
CS(O[C@@H:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[O:11][C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=1)(=O)=O.[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C)C=O>[Br:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][C@@H:7]2[CH2:8][CH2:9][CH2:10][C@@H:6]2[N:19]=[N+:20]=[N-:21])=[CH:13][CH:14]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of trans-2-(4-bromophenoxy)cyclopentyl methanesulfonate (3.52 g, 10.5 mmol) in dimethylformamide (22 mL) was added sodium azide (897 mg, 13.7 mmol) and the reaction was heated at 100° C. for 18 hours. The reaction was cooled to room temperature and partitioned between ethyl acetate and 1N aqueous lithium chloride solution. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed with saturated aqueous sodium chloride solution, dried over calcium sulfate, filtered and concentrated in vacuo to provide product as a brown oil, which was used in the next step without additional purification. Yield: 2.59 g, 9.18 mmol, 87%. 1H NMR (400 MHz, CDCl3) δ 1.65-1.73 (m, 1H), 1.89-2.05 (m, 5H), 3.74 (m, 1H), 4.66 (m, 1H), 6.83 (d, J=9.0 Hz, 2H), 7.39 (d, J=9.0 Hz, 2H).
Workup
- temperatureThe reaction was cooled to room temperature
- custompartitioned between ethyl acetate and 1N aqueous lithium chloride solution
- extractionThe aqueous layer was extracted with ethyl acetate
- washthe combined organic layers were washed with saturated aqueous sodium chloride solution
- dry with materialdried over calcium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customto provide product as a brown oil, which
- customwas used in the next step without additional purification
Sources & evidence
- ORD record
- ord-da05a31dcdce4464ad8699477f483041
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08686043B2
Reaction notes
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