Triacetoxyperiodinane → HCID 66705674, compound

HRID 425408Notes

Reaction equation

HRID 425408 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:60]=[CH:59][C:33]([CH2:34][C:35]3([C:47]([NH:49][CH2:50][CH:51]([OH:58])[CH2:52][C:53]([CH3:57])([CH3:56])[CH2:54][CH3:55])=[O:48])[CH2:39][CH2:38][CH2:37][N:36]3[C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])=[CH:32][CH:31]=2)=[N:28][CH:29]=1>ClCCl>[CH3:56][C:53]([CH3:57])([CH2:54][CH3:55])[CH2:52][C:51](=[O:58])[CH2:50][NH:49][C:47]([C:35]1([CH2:34][C:33]2[CH:59]=[CH:60][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][CH2:37][N:36]1[C:40]([O:42][C:43]([CH3:44])([CH3:45])[CH3:46])=[O:41])=[O:48]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 66705703Tert-butyl 2-[4-(5-fluoropyridin-2-yl)benzyl]-2-{[(2-hydroxy-4,4-dimethylhexyl)amino]carbonyl}pyrrolidine-1-carboxylate

Product 1

HCID 66705674HCID 66705674, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (1.08 g, 2.56 mmol) was added to an ambient temperature solution of tert-butyl 2-[4-(5-fluoropyridin-2-yl)benzyl]-2-{[(2-hydroxy-4,4-dimethylhexyl)amino]carbonyl}pyrrolidine-1-carboxylate (674 mg, 1.28 mmol) in dichloromethane (13 mL). After stirring at ambient temperature for 1 h, the reaction mixture was quenched with saturated aqueous sodium bicarbonate/saturated aqueous sodium thiosulfate (1:1) and extracted with ethyl acetate. The combined organic extracts were dried (magnesium sulfate), filtered, and concentrated in vacuo. Chromatography over silica eluting with 0-50% ethyl acetate/hexane afforded tert-butyl 2-{[(4,4-dimethyl-2-oxohexyl)amino]carbonyl}-2-[4-(5-fluoropyridin-2-yl)benzyl]pyrrolidine-1-carboxylate.

Workup

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

Sources & evidence

ORD record
ord-f296f65aa47c442ba6df4e6218b2f05e
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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