Methyl iodide → HCID 21070648, compound

HRID 1435350Notes

Reaction equation

HRID 1435350 reaction equation
[N:1]([CH:4]1[CH2:9][CH2:8][N:7]([S:10]([CH3:13])(=[O:12])=[O:11])[CH2:6][CH:5]1[OH:14])=[N+:2]=[N-:3].[H-].[Na+].[CH3:17]I>O1CCCC1>[N:1]([CH:4]1[CH2:9][CH2:8][N:7]([S:10]([CH3:13])(=[O:11])=[O:12])[CH2:6][CH:5]1[O:14][CH3:17])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21070649HCID 21070649, compound

Product 1

HCID 21070648HCID 21070648, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the stirred solution of the azide (500 mg, 2.27 mmol, Example 304) in tetrahydrofuran (8 mL) at 0° C., sodium hydride (60% in oil dispersion, 180 mg, 4.54 mmol, Aldrich) was added slowly and the mixture was stirred for 30 minutes. Methyl iodide (184 uL, 2.95 mmol, Aldrich) was then added and the mixture was stirred at room temperature overnight. The reaction was quenched with saturated ammonium chloride solution and the mixture was extracted with ethyl acetate. The extract was washed with brine and dried with sodium sulfate. The solvent was removed and the residue was purified by chromatography (15% ethyl acetate/hexanes first and then 35%) to give a yellow oil. 280 mg, 53%.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customThe reaction was quenched with saturated ammonium chloride solution
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried with sodium sulfate
  6. customThe solvent was removed
  7. customthe residue was purified by chromatography (15% ethyl acetate/hexanes first
  8. custom35%) to give a yellow oil

Sources & evidence

ORD record
ord-d7036472c37745a1aef5233dbe55db28
Source dataset
uspto-grants-2009_11
Patent number
US07615634B2

Reaction notes

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