Hydrogen Peroxide → HCID 68908267, compound

HRID 546466Notes

Reaction equation

HRID 546466 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[CH2:17][CH:16]=[CH:15][CH2:14][C@@H:13]1[NH:18][C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.[OH-:30].[Na+].OO>O1CCCC1>[CH2:22]([O:21][C:19]([NH:18][C@@H:13]1[CH2:14][CH2:15][CH:16]([OH:30])[CH2:17][C@@H:12]1[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 6331BoraneHCID 14798Sodium HydroxideHCID 13838839HCID 13838839, compound

Product 1

HCID 68908267HCID 68908267, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

cis-N1,N2-Bis(benzyloxycarbonyl)-4-cyclohexene-1,2-diamine (10 g) was dissolved in absolute tetrahydrofuran (70 ml), borane-dimethyl sulfide complex (7.4 ml) was added at 0° C., and the mixture was gradually heated to room temperature and stirred for 14 hours. Ice was added to the reaction mixture to decompose excessive borane, and a 1N aqueous solution (80 ml) of sodium hydroxide and 30% aqueous hydrogen peroxide (80 ml) were added to stir the mixture for 1 hour. 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=2:1) to obtain the title compound (9.2 g) as a colorless wax.

Workup

  1. additionborane-dimethyl sulfide complex (7.4 ml) was added at 0° C.
  2. additionIce was added to the reaction mixture
  3. stirringto stir the mixture for 1 hour
  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=2:1)

Sources & evidence

ORD record
ord-5990f54a52bc4ef09fa46676c33de282
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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