Dimethylformamide → 2-benzyl-6-[(3R,4S)-3-(fluoromethoxy)-4-methoxypyrrolidine-1-yl]-3-iodopyridine

HRID 1359347Notes

Reaction equation

HRID 1359347 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][CH2:30][F:31])[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[CH2:26][C@H:25]([O:27][CH3:28])[C@H:24]([O:29][CH2:30][F:31])[CH2:23]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 697607012-Benzyl-6-[(3r,4s)-3-(fluoromethoxy)-4-methoxypyrrolidine-1-yl]pyridine

Product 1

HCID 697586932-benzyl-6-[(3R,4S)-3-(fluoromethoxy)-4-methoxypyrrolidine-1-yl]-3-iodopyridineYield 65.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

37.4 mg of N-iodosuccinimide was added little by little to a solution containing 47.8 mg of 2-benzyl-6-[(3R,4S)-3-(fluoromethoxy)-4-methoxypyrrolidine-1-yl]pyridine obtained in Example 111 and 4.0 ml of N,N-dimethylformamide under stirring in an ice-bath, followed by stirring overnight as it was. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic phase was successively washed with an aqueous sodium thiosulfate solution, water and brine, and the solvent was removed. The residue was subjected to NH-silica gel (Fuji Silicia) chromatography and eluted with hexane/ethyl acetate (5:1) and then with hexane/ethyl acetate (3:1), to give 43.9 mg of the target compound.

Workup

  1. stirringby stirring overnight as it
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic phase was successively washed with an aqueous sodium thiosulfate solution, water and brine
  4. customthe solvent was removed
  5. washeluted with hexane/ethyl acetate (5:1)

Sources & evidence

ORD record
ord-51ae21ac50334767bfe5bd86b48897ed
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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