Triacetoxyperiodinane → HCID 21091372, compound

HRID 1349515Notes

Reaction equation

HRID 1349515 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][CH:21]([OH:35])[CH2:22][N:23]([CH3:34])[C:24](=[O:33])[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)(Cl)Cl>[Si:1]([O:18][CH2:19][CH2:20][C:21](=[O:35])[CH2:22][N:23]([CH3:34])[C:24](=[O:33])[O:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 21091371HCID 21091371, compound

Product 1

HCID 21091372HCID 21091372, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of benzyl N-[4-(tert-butyldiphenylsilanyloxy)-2-hydroxybutyl]-N-methylcarbamate (12.84 g) in chloroform (150 ml) was added 1,1,1-tris(acetoxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (Dess-Martin reagent) (15.50 g) under ice-cooling, and the mixture was stirred for 1 hr. The reaction mixture was washed successively with saturated aqueous sodium hydrogen carbonate solution, saturated aqueous sodium sulfite solution and saturated brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4) to give benzyl N-[4-(tert-butyldiphenylsilanyloxy)-2-oxobutyl]-N-methylcarbamate (10.92 g). To a solution of the obtained compound (7.95 g) in methanol (70 ml) were added methyl orthoformate (70 ml) and pyridinium p-toluenesulfonate (4.08 g) and the mixture was stirred at 60° C. for 18 hr. The reaction mixture was concentrated, and ethyl acetate was added to the residue and the precipitated solid was filtered off. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:5) to give benzyl N-[4-(tert-butyldiphenylsilanyloxy)-2,2-dimethoxybutyl]-N-methylcarbamate (2.25 g).

Workup

  1. temperaturecooling
  2. washThe reaction mixture was washed successively with saturated aqueous sodium hydrogen carbonate solution, saturated aqueous sodium sulfite solution and saturated brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-fedbfdf63f2f424a8c8855caaf14ab17
Source dataset
uspto-grants-2007_05
Patent number
US07211572B2

Reaction notes

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