Sodium Iodide → (S)-3-(4-nitrobenzoyloxy)-1-[3-(4-methoxyphenyl)propyl]pyrrolidine
Reaction equation
S(O[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)(=O)(=O)C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].[N+:25]([C:28]1[CH:41]=[CH:40][C:31]([C:32]([O:34][C@H:35]2[CH2:39][CH2:38][NH:37][CH2:36]2)=[O:33])=[CH:30][CH:29]=1)([O-:27])=[O:26]>C(#N)C>[N+:25]([C:28]1[CH:41]=[CH:40][C:31]([C:32]([O:34][C@H:35]2[CH2:39][CH2:38][N:37]([CH2:6][CH2:7][CH2:8][C:9]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=3)[CH2:36]2)=[O:33])=[CH:30][CH:29]=1)([O-:27])=[O:26]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
3-(4-Methoxyphenyl)propyl mesylate (732 mg, 3.00 mmol), sodium carbonate (320 mg, 3.00 mmol) and sodium iodide (30 mg, 0.20 mmol) were added to a solution of (S)-3-(4-nitrobenzoyloxy)pyrrolidine (472 mg, 2.00 mmol) in acetonitrile (25 ml), and they were heated under reflux at 90° C. for 6 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)-3-(4-nitrobenzoyloxy)-1-[3-(4-methoxyphenyl)propyl]pyrrolidine in the form of a light yellow oil (507 mg, 66%).
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-cffe82c9197f4fa5a798ec2e6086049d
- Source dataset
- uspto-grants-2003_03
- Patent number
- US06528504B2
Reaction notes
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