N-Iodosuccinimide → HCID 90029991, compound

HRID 1488067Notes

Reaction equation

HRID 1488067 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:15]2([OH:19])[CH2:18][O:17][CH2:16]2)[N:5]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[CH:6]=1.C1C(=O)N([I:27])C(=O)C1>C(#N)C>[I:27][C:6]1[N:5]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:13])([CH3:14])[CH3:12])[C:4]([C:15]2([OH:19])[CH2:18][O:17][CH2:16]2)=[N:3][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 90033029HCID 90033029, compound2×

Product 1

HCID 90029991HCID 90029991, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Into a 100-mL round-bottom flask, was placed a solution of 3-(4-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)oxetan-3-ol (compound 192.2, 200 mg, 0.70 mmol) in ACN (10 mL). NIS (237.7 mg, 1.06 mmol) was added to the reaction. The reaction mixture was stirred overnight at room temperature, then concentrated under reduced pressure. The reaction mixture was diluted with 40 mL of EtOAc. The organic layer was washed with 3×20 mL of brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (2:3) as eluent to furnish 100 mg (35%) of the title compound as an orange oil.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. concentrationconcentrated under reduced pressure
  3. additionThe reaction mixture was diluted with 40 mL of EtOAc
  4. washThe organic layer was washed with 3×20 mL of brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (2:3) as eluent

Sources & evidence

ORD record
ord-8a4ee06c1a5d4025a2cb717d8bfc7c55
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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