Triacetoxyperiodinane → HCID 66705623, compound

HRID 425417Notes

Reaction equation

HRID 425417 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[F:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]2[CH:54]=[CH:53][C:33]([CH2:34][C:35]3([C:41]([NH:43][CH2:44][CH:45]([OH:52])[CH2:46][C:47]([CH3:51])([CH3:50])[CH2:48][CH3:49])=[O:42])[CH2:39][CH2:38][C:37](=[O:40])[NH:36]3)=[CH:32][CH:31]=2)=[N:28][CH:29]=1>C(Cl)Cl>[CH3:50][C:47]([CH3:51])([CH2:48][CH3:49])[CH2:46][C:45](=[O:52])[CH2:44][NH:43][C:41]([C:35]1([CH2:34][C:33]2[CH:53]=[CH:54][C:30]([C:27]3[CH:26]=[CH:25][C:24]([F:23])=[CH:29][N:28]=3)=[CH:31][CH:32]=2)[CH2:39][CH2:38][C:37](=[O:40])[NH:36]1)=[O:42]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 66705633HCID 66705633, compound

Product 1

HCID 66705623HCID 66705623, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (355 mg, 0.84 m mol) was added to an ambient temperature solution of 2-[4-(5-fluoropyridin-2-yl)benzyl]-N-(2-hydroxy-4,4-dimethylhexyl)-5-oxopyrrolidine-2-carboxamide (185 mg, 0.42 mmol) in methylene chloride (5 mL). After stirring at ambient temperature for 2 hr, the reaction mixture was quenched with saturated aqueous sodium bicarbonate/saturated aqueous sodium thiosulfate (1:1) was and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (sodium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 20-60% acetone/methylene chloride afforded N-(4,4-dimethyl-2-oxohexyl)-2-[4-(5-fluoropyridin-2-yl)benzyl]-5-oxopyrrolidine-2-carboxamide.

Workup

  1. customthe reaction mixture was quenched with saturated aqueous sodium bicarbonate/saturated aqueous sodium thiosulfate (1:1)
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5eb000f7dcb24efa8b827a9877374554
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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