Methyl iodide → 526-31-8

HRID 2117014

Reaction equation

HRID 2117014 reaction equation
O[C:2]1[CH:16]=[C:15]2[C:5]([NH:6][CH:7]=[C:8]2[CH2:9][C@@H:10]([C:12]([OH:14])=[O:13])[NH2:11])=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:20]>CN(C=O)C>[CH3:20][NH:11][C@H:10]([C:12]([OH:14])=[O:13])[CH2:9][C:8]1[C:15]2[C:5](=[CH:4][CH:3]=[CH:2][CH:16]=2)[NH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 439280Oxitriptan

Product 1

HCID 160511526-31-8

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The protected tryptophan derivative from above (0.573 g, 1.00 mmol) was dissolved in DMF (3 mL) and the solution cooled in ice. Sodium hydride (60% oil dispersion, 0.048 g, 1.2 mmol) was added and the mixture stirred for 30 min. Iodomethane (0.093 mL, 1.5 mmol) was added and stirring continued for an additional hour. The reaction was then quenched with 10% citric acid (2 mL) and water (25 mL), and extracted with Et2O (100 mL). The extract was dried (MgSO4) and concentrated, and the residue purified by flash chromatography (20-30% EtOAc/hexane as eluent) to give the desired N-methyltryptophan derivative (0.284 g).

Workup

  1. temperaturethe solution cooled in ice
  2. stirringstirring
  3. waitcontinued for an additional hour
  4. customThe reaction was then quenched with 10% citric acid (2 mL) and water (25 mL)
  5. extractionextracted with Et2O (100 mL)
  6. dry with materialThe extract was dried (MgSO4)
  7. concentrationconcentrated
  8. customthe residue purified by flash chromatography (20-30% EtOAc/hexane as eluent)

Sources & evidence

ORD record
ord-4d311b15701e4abb81c142600fec6e33
Source dataset
uspto-grants-2008_10
Patent number
US07439258B2

Linked notes

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