Triethylamine → 2-benzyl-3-iodo-6-[(3S,4S)-3-(3-nitrobenzenesulfonyl)oxy-4-methoxypyrrolidin-1-yl]pyridine

HRID 1359339Notes

Reaction equation

HRID 1359339 reaction equation
C(N(CC)CC)C.[N+:8]([C:11]1[CH:12]=[C:13]([S:17](Cl)(=[O:19])=[O:18])[CH:14]=[CH:15][CH:16]=1)([O-:10])=[O:9].[CH2:21]([C:28]1[C:33]([I:34])=[CH:32][CH:31]=[C:30]([N:35]2[CH2:39][C@H:38]([O:40][CH3:41])[C@@H:37]([OH:42])[CH2:36]2)[N:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[CH2:21]([C:28]1[C:33]([I:34])=[CH:32][CH:31]=[C:30]([N:35]2[CH2:39][C@H:38]([O:40][CH3:41])[C@@H:37]([O:42][S:17]([C:13]3[CH:14]=[CH:15][CH:16]=[C:11]([N+:8]([O-:10])=[O:9])[CH:12]=3)(=[O:18])=[O:19])[CH2:36]2)[N:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 84763-Nitrobenzenesulfonyl chlorideHCID 693628352-Benzyl-3-iodo-6-[(3s,4s)-3-hydroxy-4-methoxypyrrolidine-1-yl]pyridine

Product 1

HCID 210580212-benzyl-3-iodo-6-[(3S,4S)-3-(3-nitrobenzenesulfonyl)oxy-4-methoxypyrrolidin-1-yl]pyridineYield 100.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

300 mg of 4-dimethylaminopyridine, 10 ml of triethylamine and 9.7 g of 3-nitrobenzenesulfonyl chloride were added to a solution of 10.0 g of 2-benzyl-3-iodo-6-[(3S,4S)-3-hydroxy-4-methoxypyrrolidine-1-yl]pyridine obtained in the same manner as in Example 10-c in 150 ml of ethyl acetate, followed by stirring at room temperature for 3 days. The reaction solution was first filtered through 50 g of silica gel, and washed with ethyl acetate. Further, the filtrate was filtered through 50 g of NH-silica gel and washed with ethyl acetate. The filtrate was concentrated, to give 14.6 g of the target compound.

Workup

  1. filtrationThe reaction solution was first filtered through 50 g of silica gel
  2. washwashed with ethyl acetate
  3. filtrationFurther, the filtrate was filtered through 50 g of NH-silica gel
  4. washwashed with ethyl acetate
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-5394039907654e89bd7f95d1f7ca3115
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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