Hydrogen Peroxide → HCID 68905430, compound

HRID 459526Notes

Reaction equation

HRID 459526 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH:13]=[CH:12][CH2:11][C@@H:10]1[NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-:23].[Na+].OO>O1CCCC1>[C:19]([O:18][C:16]([NH:15][C@@H:10]1[CH2:11][CH2:12][CH:13]([OH:23])[CH2:14][C@@H:9]1[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 58822264HCID 58822264, compound

Product 1

HCID 68905430HCID 68905430, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

cis-N1,N2-Bis (tert-butoxycarbonyl)-4-cyclohexene-1,2-diamine (6.1 g) was dissolved in absolute tetrahydrofuran (40 ml), and borane-dimethyl sulfide complex (2.22 ml) was added by a syringe under ice cooling. The mixture was stirred for 16 hours while gradually heating the mixture to room temperature as it is. Ice was added to the reaction mixture, and a 1N aqueous solution of sodium hydroxide and 30% aqueous hydrogen peroxide (50 ml) were added to stir the mixture at room temperature for 2 hours as it is. The reaction mixture was extracted with ethyl acetate, and the resultant organic layer was washed with saturated saline and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2→2:1) to obtain the title compound (6.1 g) as a colorless oil.

Workup

  1. additionborane-dimethyl sulfide complex (2.22 ml) was added by a syringe under ice cooling
  2. additionIce was added to the reaction mixture
  3. stirringto stir the mixture at room temperature for 2 hours as it
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. washthe resultant organic layer was washed with saturated saline
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2→2:1)

Sources & evidence

ORD record
ord-cd4e01f1cb3c4621bc71eb631e320647
Source dataset
uspto-grants-2007_03
Patent number
US07192968B2

Reaction notes

Loading…