Iodine → HCID 86675827, compound

HRID 1913523Notes

Reaction equation

HRID 1913523 reaction equation
[CH2:1]([CH:3]1[CH2:6][CH:5]([N:7]2[CH:11]=[C:10]([CH2:12][OH:13])[N:9]=[CH:8]2)[CH2:4]1)[CH3:2].C(=O)(O)[O-].[Na+].II.S([O-])([O-])(=O)=S.[Na+].[Na+]>C1(C)C=CC=CC=1.O>[CH2:1]([CH:3]1[CH2:4][CH:5]([N:7]2[CH:11]=[C:10]([CH:12]=[O:13])[N:9]=[CH:8]2)[CH2:6]1)[CH3:2]

Participants

7

Reactant 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 68247836HCID 68247836, compound

Product 1

HCID 86675827HCID 86675827, compoundYield 97.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

The compound (119 mg) obtained in Step 2 of this Reference Example was dissolved in toluene (5 mL). To this solution, a solution of sodium bicarbonate (166 mg) in water (4 mL), iodine (305 mg), and 2,2,6,6-tetramethyl-1-piperidinyloxy (11 mg) were added in this order, and the mixture was stirred at room temperature for 12 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 (115 mg, diastereomeric mixture, trans:cis=1:1). 1H-NMR (CDCl3) δ: 0.86 (1.5H, t, J=7.3 Hz), 0.90 (1.5H, t, J=7.3 Hz), 1.44 (9H, s), 1.51 (1H, dq, J=7.4, 7.4 Hz), 1.59 (1H, dq, J=7.4, 7.4 Hz), 1.87-1.97 (1H, m), 2.04-2.13 (0.5H, m), 2.28-2.38 (1.5H, m), 2.42-2.52 (1H, m), 2.66-2.75 (1H, m), 4.48 (0.5H, tt, J=9.0, 7.8 Hz), 4.72 (0.5H, tt, J=7.8, 7.4 Hz), 7.58 (0.5H, s), 7.61 (0.5H, s), 7.69 (0.5H, s), 7.74 (0.5H, s), 9.87 (0.5H, s), 9.88 (0.5H, s).

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-5587165a75b64514bca6d299421dd514
Source dataset
uspto-grants-2013_12
Patent number
US08609710B2

Reaction notes

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