Boron tribromide → HCID 19029813, compound

HRID 2256377Notes

Reaction equation

HRID 2256377 reaction equation
[CH3:1][C:2]1([CH2:20][OH:21])[CH:15]2[C:6]([CH3:18])([C:7]3[C:12]([CH2:13][CH2:14]2)=[C:11]([O:16]C)[CH:10]=[CH:9][CH:8]=3)[CH2:5][CH2:4][C:3]1=[O:19].B(Br)(Br)Br.C(=O)([O-])[OH:27].[Na+]>ClCCl.CCCCCC>[OH:21][CH2:20][C:2]1([CH3:1])[CH:15]2[C:6]([CH3:18])([C:7]3[C:8](=[O:27])[CH:9]=[CH:10][C:11](=[O:16])[C:12]=3[CH2:13][CH2:14]2)[CH2:5][CH2:4][C:3]1=[O:19]

Participants

6

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 19029820HCID 19029820, compound

Product 1

HCID 19029813HCID 19029813, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

In 4 ml of dichloromethane was dissolved 150 mg of the compound obtained in Example 8, and under ice-cooling, 1.2 ml of a solution (1.0M) of boron tribromide in n-hexane was added. The mixture was stirred at 0° C. for 1.5 hours, and then it was diluted with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated. In 10 ml of ethanol was dissolved 34 mg of the resulting crude crystals, and after addition of an aqueous solution (6.8 ml) containing 83 mg of potassium dinitrosulfonate and 34 mg of dipotassium hydrogen phosphate, the mixture was stirred at room temperature for 13 hours. The reaction mixture was then diluted with water and extracted with chloroform. The organic layer was washed with saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. The resulting crude product was purified by silica gel column chromatography (eluent=ethyl acetate:n-hexane=1:9) to provide 1 mg of the object compound.

Workup

  1. temperatureunder ice-cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. dissolutionIn 10 ml of ethanol was dissolved 34 mg of the resulting crude crystals
  7. additionafter addition of an aqueous solution (6.8 ml)
  8. additioncontaining 83 mg of potassium dinitrosulfonate and 34 mg of dipotassium hydrogen phosphate
  9. stirringthe mixture was stirred at room temperature for 13 hours
  10. additionThe reaction mixture was then diluted with water
  11. extractionextracted with chloroform
  12. washThe organic layer was washed with saturated sodium chloride solution
  13. dry with materialdried over magnesium sulfate
  14. concentrationconcentrated
  15. customThe resulting crude product was purified by silica gel column chromatography (eluent=ethyl acetate:n-hexane=1:9)

Sources & evidence

ORD record
ord-5078208fea3a46d586c96eda11cdb100
Source dataset
uspto-grants-1997_08
Patent number
US05654343

Reaction notes

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