Iodine → HCID 178461291, compound

HRID 1913518Notes

Reaction equation

HRID 1913518 reaction equation
[CH3:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[CH:12]=[C:11]([CH2:13][OH:14])[N:10]=[CH:9]2)[CH2:4][CH2:3]1.C(=O)(O)[O-].[Na+].II.S([O-])([O-])(=O)=S.[Na+].[Na+]>C1(C)C=CC=CC=1.O>[CH3:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([N:8]2[CH:12]=[C:11]([CH:13]=[O:14])[N:10]=[CH:9]2)[CH2:6][CH2:7]1

Participants

7

Reactant 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 178461292HCID 178461292, compound

Product 1

HCID 178461291HCID 178461291, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

The compound (1.04 g) obtained in Step 2 of this Reference Example was dissolved in toluene (10 mL). To the solution, a solution of sodium bicarbonate (1.35 g) in water (5 mL), iodine (2.72 g), and 2,2,6,6-tetramethyl-1-piperidinyloxy (84 mg) were added in this order, and the mixture was stirred at room temperature for 2 hours. To the reaction solution, saturated aqueous sodium thiosulfate was added, and organic matter was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered, and the solvent was distilled off under reduced pressure to obtain a crude product. This crude product was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=1/1-1/2) to obtain the title compound (0.900 g).

Workup

  1. extractionorganic matter was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. distillationthe solvent was distilled off under reduced pressure
  5. customto obtain a crude product
  6. customThis crude product was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=1/1-1/2)

Sources & evidence

ORD record
ord-1b85374c21d04779a039cab6fb0cc3bb
Source dataset
uspto-grants-2013_12
Patent number
US08609710B2

Reaction notes

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