Sodium Iodide → (S)-1-(4-chlorophenethyl)-3-(4-nitrobenzoyloxy)pyrrolidine
Reaction equation
S(C1C=CC(C)=CC=1)(O[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].[N+:29]([C:32]1[CH:45]=[CH:44][C:35]([C:36]([O:38][C@H:39]2[CH2:43][CH2:42][NH:41][CH2:40]2)=[O:37])=[CH:34][CH:33]=1)([O-:31])=[O:30]>C(#N)C>[Cl:13][C:10]1[CH:9]=[CH:8][C:7]([CH2:6][CH2:5][N:41]2[CH2:42][CH2:43][C@H:39]([O:38][C:36](=[O:37])[C:35]3[CH:34]=[CH:33][C:32]([N+:29]([O-:31])=[O:30])=[CH:45][CH:44]=3)[CH2:40]2)=[CH:12][CH:11]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
4-Chlorophenethyl tosylate (683 mg, 2.20 mmol), sodium carbonate (236 mg, 2.20 mmol) and sodium iodide (20 mg, 0.13 mmol) were added to a solution of (S)-3-(4-nitrobenzoyloxy)pyrrolidine (472 mg, 2.00 mmol) in acetonitrile (10 ml), and they were heated under reflux at 90° C. for 8 hours. The solvent was evaporated under reduced pressure. The obtained residue was subjected to silica gel column chromatography. The product was eluted with hexane and ethyl acetate (10:1) and then with a mixture of the same solvents (1:1). The appropriate fractions were combined, and the solvent was evaporated under reduced pressure to obtain (S)-1-(4-chlorophenethyl)-3-(4-nitrobenzoyloxy)pyrrolidine in the form of a light yellow oil (315 mg, 42%).
Workup
- temperaturewere heated
- customThe solvent was evaporated under reduced pressure
- washThe product was eluted with hexane and ethyl acetate (10:1)
- additionwith a mixture of the same solvents (1:1)
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-36e4c4f37a4640498373893b0352db85
- Source dataset
- uspto-grants-2003_03
- Patent number
- US06528504B2
Reaction notes
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