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Sodium Iodide → (S)-3-(4-Nitrobenzoyloxy)-1-(4-methoxyphenethyl)pyrrolidine

HRID 1859444
Notes
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Reaction equation

HRID 1859444 reaction equation
S(C1C=CC(C)=CC=1)(O[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].[N+:30]([C:33]1[CH:46]=[CH:45][C:36]([C:37]([O:39][C@H:40]2[CH2:44][CH2:43][NH:42][CH2:41]2)=[O:38])=[CH:35][CH:34]=1)([O-:32])=[O:31]>C(#N)C>[N+:30]([C:33]1[CH:46]=[CH:45][C:36]([C:37]([O:39][C@H:40]2[CH2:44][CH2:43][N:42]([CH2:5][CH2:6][C:7]3[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=3)[CH2:41]2)=[O:38])=[CH:35][CH:34]=1)([O-:32])=[O:31]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 2853842-(4-Methoxyphenyl)ethyl 4-methylbenzenesulfonateHCID 12148704(S)-3-(4-nitrobenzoyloxy)pyrrolidine

Product 1

HCID 69901303(S)-3-(4-Nitrobenzoyloxy)-1-(4-methoxyphenethyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
90 °C

Procedure

4-Methoxyphenethyl tosylate (1.24 g, 4.05 mmol), sodium carbonate (430 mg, 4.06 mmol) and sodium iodide (40 mg, 0.26 mmol) were added to a solution of (S)-3-(4-nitrobenzoyloxy)pyrrolidine (799 mg, 3.38 mmol) in acetonitrile (40 ml), and they were heated under reflux at 90° C. for 3 hours. The insoluble material was removed by the filtration. The insoluble material was washed with ethyl acetate, and the wash solution was combined with the filtrate. 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-(4-methoxy-phenethyl)pyrrolidine in the form of a light yellow oil (1.00 g, 80%).

Workup

  1. temperaturewere heated
  2. customThe insoluble material was removed by the filtration
  3. washThe insoluble material was washed with ethyl acetate
  4. customThe solvent was evaporated under reduced pressure
  5. washThe product was eluted with hexane and ethyl acetate (10:1)
  6. additionwith a mixture of the same solvents (1:1)
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-aaf43faa9e074a3eba372d6a44c7e83b
Source dataset
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06528504B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes