Acetic Acid → 2-Benzyl-3-iodo-6-[(3S,4S)-3-acetoxy-4-methoxypyrrolidine-1-yl)pyridine

HRID 1359340Notes

Reaction equation

HRID 1359340 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:11]([C:18]1[C:23]([I:24])=[CH:22][CH:21]=[C:20]([N:25]2[CH2:29][C@H:28]([O:30][CH3:31])[C@@H:27](OS(C3C=CC=C([N+]([O-])=O)C=3)(=O)=O)[CH2:26]2)[N:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CS(C)=O>[CH2:11]([C:18]1[C:23]([I:24])=[CH:22][CH:21]=[C:20]([N:25]2[CH2:29][C@H:28]([O:30][CH3:31])[C@@H:27]([O:3][C:1](=[O:4])[CH3:2])[CH2:26]2)[N:19]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10796Cesium carbonateHCID 210580212-benzyl-3-iodo-6-[(3S,4S)-3-(3-nitrobenzenesulfonyl)oxy-4-methoxypyrrolidin-1-yl]pyridine

Product 1

HCID 1317239962-Benzyl-3-iodo-6-[(3S,4S)-3-acetoxy-4-methoxypyrrolidine-1-yl)pyridine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

4.2 ml of acetic acid was added to a mixture of 7.9 g of cesium carbonate and 15 ml of dimethyl sulfoxide. After foaming stopped, a mixture of 14.4 g of 2-benzyl-3-iodo-6-[(3S,4S)-3-(3-nitrobenzenesulfonyl)oxy-4-methoxypyrrolidine-1-yl]pyridine and 35 ml of dimethyl sulfoxide was added thereto, followed by heating under stirring for 6 hours in an oil bath kept at 70° C. in a nitrogen atmosphere. The reaction solution was cooled and then subjected to extraction with ethyl acetate-water. The organic phase was washed with water and brine brine, dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography using 10-15% ethyl acetate/hexane, to give 7.5 g of the target compound.

Workup

  1. additionwas added
  2. temperatureby heating
  3. customkept at 70° C. in a nitrogen atmosphere
  4. temperatureThe reaction solution was cooled
  5. extractionsubjected to extraction with ethyl acetate-water
  6. washThe organic phase was washed with water and brine brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1e6587ff034f47f3b2b7f34f4a7b2dcf
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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