Triacetoxyperiodinane → HCID 57785903, compound

HRID 1628922Notes

Reaction equation

HRID 1628922 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=4[Cl:22])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH:23]([CH2:27][CH3:28])[CH:24]([OH:26])[CH3:25])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(#N)C.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=4[Cl:22])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH:23]([CH2:27][CH3:28])[C:24](=[O:26])[CH3:25])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57786321HCID 57786321, compound

Product 1

HCID 57785903HCID 57785903, compoundYield 88.2%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 24477Sodium ThiosulfateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 3-[9-chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]pentan-2-ol (234 mg, 0.533 mmol) in acetonitrile (5 mL) was added Dess-Martin reagent (271 mg, 0.639 mmol) at 0° C., and the resultant mixture was stirred at room temperature for 1 h and diluted with aqueous sodium bicarbonate and aqueous sodium thiosulfate. The resultant mixture was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 20-50% ethyl acetate/n-hexane gradient mixture to give the title compound as a colorless amorphous solid (205 mg, 0.470 mmol, 88%).

Workup

  1. extractionThe resultant mixture was extracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel eluting with a 20-50% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-b16385986e604fd3a550f45306cf9f19
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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