Hydrogen Peroxide → 3-(1-((4-iodo-5-methyl-1H-pyrazol-1-yl)methyl)cycloheptyloxy)propan-1-ol

HRID 1778896Notes

Reaction equation

HRID 1778896 reaction equation
[CH2:1]([O:4][C:5]1([CH2:12][N:13]2[C:17]([CH3:18])=[C:16]([I:19])[CH:15]=[N:14]2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)[CH:2]=[CH2:3].C12BC(CCC1)CCC2.[O:29]1CCCC1.[OH-].[Na+].OO>O1CCCC1>[I:19][C:16]1[CH:15]=[N:14][N:13]([CH2:12][C:5]2([O:4][CH2:1][CH2:2][CH2:3][OH:29])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[C:17]=1[CH3:18]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 894983011-((1-(allyloxy)cycloheptyl)methyl)-4-iodo-5-methyl-1H-pyrazoleHCID 178419114HCID 178419114, compound

Product 1

HCID 894984103-(1-((4-iodo-5-methyl-1H-pyrazol-1-yl)methyl)cycloheptyloxy)propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of EXAMPLE 155A (1.7 g) in tetrahydrofuran (20 mL) was added a 0.5 M 9-borabicyclo[3.3.1]nonane-tetrahydrofuran solution (50 mL, 0.5 M) at 0° C. After the reaction mixture was stirred for 24 hours at room temperature, a 0.5 M NaOH aqueous solution (30 mL) and 30% H2O2 aqueous solution (5.5 mL) were added. After the reaction mixture was stirred for 16 hours, the reaction was then quenched by adding water (15 mL). The reaction mixture was extracted with ethyl acetate, and the organic layer was washed with water and a saturated aqueous NaCl solution. After the organic layer was dried over Na2SO4, and filtered, the solvent was evaporated under reduced pressure. The crude product was purified on a silica gel column, eluting with 10-50% ethyl acetate in hexanes, to provide the title compound.

Workup

  1. stirringAfter the reaction mixture was stirred for 16 hours
  2. customthe reaction was then quenched
  3. additionby adding water (15 mL)
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. washthe organic layer was washed with water
  6. dry with materialAfter the organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure
  9. customThe crude product was purified on a silica gel column
  10. washeluting with 10-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-54ecc8f7871e4090a5060bcacd812d07
Source dataset
uspto-grants-2016_02
Patent number
US09266877B2

Reaction notes

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