Hydrogen Peroxide → HCID 22064361, compound

HRID 1827870Notes

Reaction equation

HRID 1827870 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]2[CH2:13][CH:12]=[CH:11][CH2:10]2)=[C:4]([N+:14]([O-:16])=[O:15])[CH:3]=1.B1C2CCCC1CCC2.[OH-:26].[Na+].OO>C1COCC1.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]2[CH2:10][CH2:11][CH:12]([OH:26])[CH2:13]2)=[C:4]([N+:14]([O-:16])=[O:15])[CH:3]=1

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 22064360HCID 22064360, compound

Product 1

HCID 22064361HCID 22064361, compoundYield 42.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Example 25A (1.18 g, 5 mmol) in THF (20 mL) was treated with a solution of 9-BBN (0.5M in THF, 10 mL, 5.0 mmol) via syringe. After stirring at room temperature overnight, the solution was cooled with an ice bath, treated with a solution of NaOH (0.2 g) in water (2 mL), treated dropwise with hydrogen peroxide (30% wt, 0.56 g, 5.0 mmol), and stirred for 3 hours. The mixture was treated with water (50 mL) and ethyl acetate (150 mL) and the organic phase was extracted with ethyl acetate. The combined organic extracts were dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 60% ethyl acetate/hexanes to provide 0.55 g (42.8%) of the desired product. MS (DCI/NH3) m/z 275 (M+NH4)+; 1H NMR indicated two isomers in ˜4:1 ratio. The spectrum of the major isomer (300 MHz, CDCl3) δ 7.79 (d, J=2.4 Hz, 1H), 7.46 (dd, J=8.8, 2.7 Hz, 1H), 7.01 (d, J=8.8 Hz, 1H), 4.95–5.05 (m, 1H), 4.55–4.60 (m, 1H), 1.4–2.30 (m, 7H).

Workup

  1. temperaturethe solution was cooled with an ice bath
  2. stirring0.56 g, 5.0 mmol), and stirred for 3 hours
  3. extractionthe organic phase was extracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash column chromatography on silica gel with 60% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-2b60c9cc2ef74b03912148e10ff874be
Source dataset
uspto-grants-2006_06
Patent number
US07056925B2

Reaction notes

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