Methyl iodide → HCID 89498100, compound

HRID 1430304Notes

Reaction equation

HRID 1430304 reaction equation
[N:1]([CH2:4][C:5]1([OH:13])[CH2:10][CH2:9][CH2:8][C:7]([CH3:12])([CH3:11])[CH2:6]1)=[N+:2]=[N-:3].[H-].[Na+].[CH3:16]I>O1CCCC1>[N:1]([CH2:4][C:5]1([O:13][CH3:16])[CH2:10][CH2:9][CH2:8][C:7]([CH3:11])([CH3:12])[CH2:6]1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 60154003HCID 60154003, compound

Product 1

HCID 89498100HCID 89498100, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of EXAMPLE 166B (1.33 g) was added dropwise to a suspension of NaH (60% dispersion in mineral oil, 435 mg) in tetrahydrofuran (15 mL) at 0° C. The mixture was stirred for 10 minutes at 0° C. and for 30 minutes at room temperature. CH3I (1.55 g) was added dropwise. The resulting reaction mixture was stirred overnight at rom temperature, and then quenched with water (100 mL) and extracted with ethyl acetate (3×50 mL). The extracts were washed with brine, dried (Na2SO4), and filtered. After concentration, the crude material was purified by flash chromatography on silica gel using 0 to 7% ethyl acetate in hexanes to afford the title compound.

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred overnight at rom temperature
  3. customquenched with water (100 mL)
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. washThe extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationAfter concentration
  9. customthe crude material was purified by flash chromatography on silica gel using 0 to 7% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-b01b501a22eb4073a88d04b96c630453
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

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