N-Iodosuccinimide → HCID 86702096, compound

HRID 715837Notes

Reaction equation

HRID 715837 reaction equation
[CH3:1][C:2]12[CH2:12][C:6]3([CH2:13][N:14]4[C:18]([CH3:19])=[CH:17][CH:16]=[N:15]4)[CH2:7][C:8]([CH3:11])([CH2:10][C:4]([O:20][CH2:21][CH2:22][OH:23])([CH2:5]3)[CH2:3]1)[CH2:9]2.[I:24]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)(=O)C>[CH3:1][C:2]12[CH2:3][C:4]3([O:20][CH2:21][CH2:22][OH:23])[CH2:10][C:8]([CH3:11])([CH2:7][C:6]([CH2:13][N:14]4[C:18]([CH3:19])=[C:17]([I:24])[CH:16]=[N:15]4)([CH2:5]3)[CH2:12]1)[CH2:9]2

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 86702094HCID 86702094, compound

Product 1

HCID 86702096HCID 86702096, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the 2-({3,5-dimethyl-7-[(5-methyl-1H-pyrazol-1-yl)methyl]tricyclo[3.3.1.13,7]dec-1-yl}oxy)ethanol (3.5 g, 11 mmol) in N,N-dimethylformamide (30 ml) was added N-iodosuccinimide (3.2 g, 14.22 mmol). The mixture was stirred at room temperature for 1.5 hours. The reaction mixture was then diluted with ethyl acetate and washed with aqueous sodium thiosulfate, water and brine. After drying over anhydrous sodium sulfate, the mixture was filtered and concentrated. The residue was purified by normal phase chromatography to give the title compound.

Workup

  1. washwashed with aqueous sodium thiosulfate, water and brine
  2. dry with materialAfter drying over anhydrous sodium sulfate
  3. filtrationthe mixture was filtered
  4. concentrationconcentrated
  5. customThe residue was purified by normal phase chromatography

Sources & evidence

ORD record
ord-54433c1596ea48a39b8e9025a404ba9e
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Reaction notes

Loading…