Dimethylformamide → HCID 69758739, compound

HRID 1359364Notes

Reaction equation

HRID 1359364 reaction equation
[I:1]N1C(=O)CCC1=O.[CH2:9]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([N:22]2[CH2:26][C@H:25]([O:27][CH3:28])[C@H:24]([O:29][CH3:30])[CH2:23]2)[N:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CN(C)C=O>O>[CH2:9]([C:16]1[C:21]([I:1])=[CH:20][CH:19]=[C:18]([N:22]2[CH2:23][C@H:24]([O:29][CH3:30])[C@H:25]([O:27][CH3:28])[CH2:26]2)[N:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 120273N-IodosuccinimideHCID 69758678HCID 69758678, compound

Product 1

HCID 69758739HCID 69758739, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

708 mg of N-iodosuccinimide was added little by little to a mixture of 783 mg of 2-benzyl-6-(cis-3,4-dimethoxypyrrolidine-1-yl)pyridine and 7.0 ml of N,N-dimethylformamide under ice-cooling, followed by stirring overnight as it was. The reaction solution was poured into water and extracted with ethyl acetate. The organic phase was washed with sodium thiosulfate, water and brine, and the solvent was removed. Then, the residue was subjected to NH-silica gel (Fuji Silicia) column chromatography and eluted with hexane/ethyl acetate (5:1) and then with hexane/ethyl acetate (3:1), to give 995 mg of the target compound.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with sodium thiosulfate, water and brine
  4. customthe solvent was removed
  5. washeluted with hexane/ethyl acetate (5:1)

Sources & evidence

ORD record
ord-c95f5afe59c04780b903f073cb3b87fb
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

Loading…