Potassium Iodide → HCID 15671511, compound

HRID 2371400Notes

Reaction equation

HRID 2371400 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:13][C@H:12]1[CH2:24]OS(C)(=O)=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-:30].[K+]>CC(CC)=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:13][C@H:12]1[CH2:24][I:30])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4875Potassium IodideHCID 15671507HCID 15671507, compound

Product 1

HCID 15671511HCID 15671511, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of (2S,4R)-1-benzyloxycarbonyl-2-methylsulfonyloxymethyl-4-t-butyldimethylsilyloxypyrrolidine (108.5 g) in methylethylketone (1100 ml), potassium iodide (73.5 g) was added, and the resultant mixture was refluxed for 3 hours. The reaction mixture was filtered, and the filtrate was concentrated to remove the solvent. The residue was diluted with ethyl acetate, washed with aqueous sodium chloride solution, aqueous sodium hypochlorite solution and aqueous sodium chloride solution in order and dried over magnesium sulfate. Removal of the solvent gave (2S,4R)-1-benzyloxycarbonyl-2-iodomethyl-4-t-butyldimethylsilyloxypyrrolidine.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customto remove the solvent
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed with aqueous sodium chloride solution, aqueous sodium hypochlorite solution and aqueous sodium chloride solution in order
  6. dry with materialdried over magnesium sulfate
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-1672c47cb3ee4a61a751862acb422b24
Source dataset
uspto-grants-1992_03
Patent number
US05093328

Reaction notes

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