Sodium Iodide → HCID 14830190, compound

HRID 1088254Notes

Reaction equation

HRID 1088254 reaction equation
[N+:1]([C:4]1[CH:39]=[CH:38][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@H:15]([O:17][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14][C@H:13]2[CH2:26]OS(C2C=CC(C)=CC=2)(=O)=O)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[I-:40].[Na+]>CC(CC)=O>[N+:1]([C:4]1[CH:39]=[CH:38][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@H:15]([O:17][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14][C@H:13]2[CH2:26][I:40])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 14830188HCID 14830188, compound

Product 1

HCID 14830190HCID 14830190, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

(2S,4R)-1-(p-Nitrobenzyloxycarbonyl)-2-p-toluenesulfonyloxymethyl-4-benzoyloxypyrrolidine (35.82 g) was dissolved in 90 ml of methylethylketone, and 19.29 g of sodium iodide was added thereto, followed by stirring under reflux for 1 hour. The reaction mixture was cooled down to room temperature and filtered. The filtrate was distilled to remove the solvent. The residue was diluted with ethyl acetate, washed successively with water, a sodium hypochlorite solution and water and dried over anhydrous sodium sulfate. The solvent was removed by distillation to give (2S,4R)-1-(p-nitrobenzyloxycarbonyl)-2-iodomethyl-4-benzoyloxypyrrolidine.

Workup

  1. temperatureunder reflux for 1 hour
  2. filtrationfiltered
  3. distillationThe filtrate was distilled
  4. customto remove the solvent
  5. additionThe residue was diluted with ethyl acetate
  6. washwashed successively with water
  7. dry with materiala sodium hypochlorite solution and water and dried over anhydrous sodium sulfate
  8. customThe solvent was removed by distillation

Sources & evidence

ORD record
ord-0d04bf86bfb9420892f940ffa628d549
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

Loading…