Hydrogen Peroxide → HCID 86683180, compound

HRID 1852076Notes

Reaction equation

HRID 1852076 reaction equation
[CH2:1]([C:4]1[N:5]=[C:6]([Cl:15])[C:7]2[C:12]([C:13]=1[OH:14])=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:2]=[CH2:3].B1C2CCCC1CCC2.[OH-:25].[Na+].OO>O1CCCC1>[Cl:15][C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:13]([OH:14])=[C:4]([CH2:1][CH2:2][CH2:3][OH:25])[N:5]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 86683179HCID 86683179, compound

Product 1

HCID 86683180HCID 86683180, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 3-allyl-1-chloroisoquinolin-4-ol (670 mg, 3.05 mmol) in dry tetrahydrofuran (5 mL) at room temperature was added 0.5 M in THF solution of 9-BBN (18.30 mL, 9.15 mmol) and the mixture was stirred for overnight. 3N NaOH (9.15 mL, 27.5 mmol) and H2O2 (2.83 mL, 30.5 mmol) were then added to the mixture. The mixture was stirred for 45 min before quenching with sat. NaCl solution. 1 N HCl was then added to the solution to adjust PH<7. The reaction was extracted with EtOAc. The organic layer was washed with brine, dried and concentrated to afford a yellow oil that was purified by silica gel chromatography using 20-40% EtOAc/hexane to obtain 1-chloro-3-(3-hydroxypropyl)isoquinolin-4-ol (520 mg, 70%) as product. MS: MS m/z 238.0 (M++1).

Workup

  1. stirringThe mixture was stirred for 45 min
  2. custombefore quenching with sat. NaCl solution
  3. addition1 N HCl was then added to the solution
  4. extractionThe reaction was extracted with EtOAc
  5. washThe organic layer was washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customto afford a yellow oil that
  9. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-9f156566c16642eeb9830a96e23c707d
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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