Sodium Thiosulfate → HCID 86591774, compound

HRID 2216381Notes

Reaction equation

HRID 2216381 reaction equation
[I:1]N1C(=O)CCC1=O.[CH2:9]([C:16]1[CH:17]=[C:18]([N:22]2[CH2:26][C@H:25]([O:27][CH3:28])[C@H:24]([O:29][CH3:30])[CH2:23]2)[CH:19]=[CH:20][CH:21]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C)C=O>[CH2:9]([C:16]1[CH:17]=[C:18]([N:22]2[CH2:26][CH:25]([O:27][CH3:28])[CH:24]([O:29][CH3:30])[CH2:23]2)[CH:19]=[CH:20][C:21]=1[I:1])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 69360909HCID 69360909, compound

Product 1

HCID 86591774HCID 86591774, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under ice-cooling, 227 mg of N-iodosuccinimide was added to a mixture of 250 mg of (3R,4S)-1-(3-benzylphenyl)-3,4-dimethoxypyrrolidine (Production Example 11) and 3 ml of N,N-dimethylformamide, followed by stirring at the same temperature for 2 hours. 0.5 ml of a 1 M aqueous solution of sodium thiosulfate was added to the reaction mixture, and then the mixture was extracted with ethyl acetate/water. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and then evaporated. The residue was subjected to silica gel column chromatography with 10% ethyl acetate/hexane, to give 340 mg of (3R,4S)-1-(3-benzyl-4-iodophenyl-3,4-dimethoxypyrrolidine.

Workup

  1. temperatureUnder ice-cooling
  2. extractionthe mixture was extracted with ethyl acetate/water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-828f09457f37434486cfe305e2e1a530
Source dataset
uspto-grants-2006_09
Patent number
US07112593B2

Reaction notes

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