Methyl iodide → HCID 89863191, compound

HRID 627154Notes

Reaction equation

HRID 627154 reaction equation
[CH2:1]([O:4][N:5]1[C:11](=[O:12])[N:10]2[CH2:13][CH:6]1[C:7]([CH2:16][O:17][CH3:18])=[CH:8][C@H:9]2[CH2:14][OH:15])[CH:2]=[CH2:3].I[CH3:20].[Al]>C(#N)C.[Ag]=O>[CH2:1]([O:4][N:5]1[C:11](=[O:12])[N:10]2[CH2:13][CH:6]1[C:7]([CH2:16][O:17][CH3:18])=[CH:8][C@H:9]2[CH2:14][O:15][CH3:20])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 5359268AluminumHCID 117940148HCID 117940148, compound

Product 1

HCID 89863191HCID 89863191, compoundYield 31.6%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of Intermediate 123 (0.3 g, 1.18 mmol) in ACN (12 mL) was added iodomethane (0.734 mL, 11.80 mmol) and silver oxide (1.094 g, 4.72 mmol). The reaction was stirred at rt with aluminum foil wrapped around overnight. LCMS showed product. The mixture was filtered and concentrated. The residue was then purified by silica gel column (40 g, 0-100% Hex/EA) to afford the title compound (0.100 g, 31.6%) as an oil.

Workup

  1. waitwrapped around overnight
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. customThe residue was then purified by silica gel column (40 g, 0-100% Hex/EA)

Sources & evidence

ORD record
ord-16461e0d21d144329adc5b07f2e7d770
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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