Water → HCID 18678527, compound

HRID 1634740Notes

Reaction equation

HRID 1634740 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:18][CH2:17][CH:16]([CH2:19][OH:20])[CH2:15][CH2:14]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].O>CS(C)=O.C1COCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([N:13]2[CH2:18][CH2:17][CH:16]([CH:19]=[O:20])[CH2:15][CH2:14]2)(=[O:11])=[O:12])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 962WaterHCID 18678701HCID 18678701, compound

Product 1

HCID 18678527HCID 18678527, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-hydroxy-1,2-benziodooxol-3(1H)-one-1-oxide (IBX) (8.73 g, 3.12 mmol) in DMSO (30 mL) and THF (15 mL) was stirred at room temperature over a period of 20 minutes. In one portion [1-(4-Nitro-benzenesulfonyl)-piperidin-4-yl]-methanol (4.69 g, 15.6 mmol) was added and the solution heated to 50° C. Water was added to the reaction until a white precipitate formed. The reaction mixture was filtered and washed with ethyl acetate. The filtrate was partitioned with ethyl acetate and water. The organic phase was dried (sodium sulfate) and concentrated in vacuo to give 4.32 g of the product as a tan solid

Workup

  1. temperaturethe solution heated to 50° C
  2. customformed
  3. filtrationThe reaction mixture was filtered
  4. washwashed with ethyl acetate
  5. customThe filtrate was partitioned with ethyl acetate and water
  6. dry with materialThe organic phase was dried (sodium sulfate)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a140383a901a4ef89754b4cfd7ff1dea
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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