Triacetoxyperiodinane → HCID 57785883, compound

HRID 1399115Notes

Reaction equation

HRID 1399115 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH:23]1([CH:26]([C:28]2[C:33]3[N:34]4[CH2:40][CH2:39][CH2:38][N:37]([C:41]5[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][C:42]=5[Cl:48])[C:35]4=[N:36][C:32]=3[CH:31]=[CH:30][CH:29]=2)[OH:27])[CH2:25][CH2:24]1>ClCCl.C(=O)([O-])O.[Na+]>[CH:23]1([C:26]([C:28]2[C:33]3[N:34]4[CH2:40][CH2:39][CH2:38][N:37]([C:41]5[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][C:42]=5[Cl:48])[C:35]4=[N:36][C:32]=3[CH:31]=[CH:30][CH:29]=2)=[O:27])[CH2:25][CH2:24]1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57785945HCID 57785945, compound

Product 1

HCID 57785883HCID 57785883, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

Dess-Martin reagent (925 mg, 2.18 mmol) was added to a stirred solution of cyclopropyl[1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a ]benzimidazol-6-yl]methanol (770 mg, 1.98 mmol) in dichloromethane (8.0 mL) at 0 ° C., and the mixture was stirred at 0 ° C. for 90 min. The mixture was diluted with saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 5-50% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the solid, which was recrystallized from ethyl acetate/diisopropyl ether to give the title compound as a colorless crystal (226 mg, 0.585 mmol, 30%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel eluting with a 5-50% ethyl acetate/n-hexane gradient mixture
  7. concentrationThe filtrate was concentrated in vacuo
  8. customto give the solid, which
  9. customwas recrystallized from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-beb46ada8c5849cdb9f39f6269011f99
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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