Hydrogen Peroxide → HCID 57657248, compound

HRID 244831Notes

Reaction equation

HRID 244831 reaction equation
[CH2:1]([N:5]1[C:17]2[C:16]3[CH:15]=[C:14]([CH:18]=[CH2:19])[CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:20])[C:8]=2[N:7]=[CH:6]1)[CH:2]([CH3:4])[CH3:3].C12BC(CCC1)CCC2.[OH:30]O.[OH-].[Na+]>O.O1CCCC1>[NH2:20][C:9]1[C:8]2[N:7]=[CH:6][N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[C:17]=2[C:16]2[CH:15]=[C:14]([CH2:18][CH2:19][OH:30])[CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonane2×HCID 21984387HCID 21984387, compound

Product 1

HCID 57657248HCID 57657248, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A 500 mL round bottom flask was charged with 1-isobutyl-8-vinyl-1H-imidazo[4,5-c]quinolin-4-amine (850 mg, 3.2 mmol) and 200 mL of tetrahydrofuran. The flask was purged with nitrogen. A solution of 9-borabicyclo[3.3.1]nonane (0.5M in tetrahydrofuran, 8.5 mL, 4.25 mmol) was added in one portion and the reaction was stirred overnight. Additional 9-borabicyclo[3.3.1]nonane (0.5M in tetrahydrofuran, 12.5 mL, 6.25 mmol) was added and the mixture was stirred for approximately 24 hours. The reaction was cooled to 0° C. with an ice/water bath and 30% H2O2 (2 mL) was added dropwise. After 5 minutes, 10% NaOH (5 mL) was added dropwise. The reaction was stirred for 30 minutes, diluted with water (100 mL) and then extracted with chloroform (3×100 mL). The combined organic fractions were concentrated under reduced pressure and purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a gradient of 0-30% CMA in chloroform) followed by recrystallization from acetonitrile to provide 580 mg of 2-(4-amino-1-isobutyl-1H-imidazo[4,5-c]quinolin-8-yl)ethanol as an off-white solid, mp 214-216° C.

Workup

  1. customThe flask was purged with nitrogen
  2. stirringthe mixture was stirred for approximately 24 hours
  3. waitAfter 5 minutes
  4. stirringThe reaction was stirred for 30 minutes
  5. extractionextracted with chloroform (3×100 mL)
  6. concentrationThe combined organic fractions were concentrated under reduced pressure
  7. custompurified by chromatography
  8. washeluting with a gradient of 0-30% CMA in chloroform)
  9. customfollowed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-5fe8906970b443b98bcef281b886d7aa
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

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