Triacetoxyperiodinane → Tert-butyl 2-{[(4,4-dimethyl-2-oxohexyl)amino]carbonyl}-4,4-difluoro-2-[4-(5-fluoropyridin-2-yl)benzyl]pyrrolidine-1-carboxylate

HRID 1881498Notes

Reaction equation

HRID 1881498 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[F:23][C:24]1([F:62])[CH2:28][N:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:26]([CH2:48][C:49]2[CH:54]=[CH:53][C:52]([C:55]3[CH:60]=[CH:59][C:58]([F:61])=[CH:57][N:56]=3)=[CH:51][CH:50]=2)([C:36]([NH:38][CH2:39][CH:40]([OH:47])[CH2:41][C:42]([CH3:46])([CH3:45])[CH2:43][CH3:44])=[O:37])[CH2:25]1>ClCCl>[CH3:45][C:42]([CH3:46])([CH2:43][CH3:44])[CH2:41][C:40](=[O:47])[CH2:39][NH:38][C:36]([C:26]1([CH2:48][C:49]2[CH:50]=[CH:51][C:52]([C:55]3[CH:60]=[CH:59][C:58]([F:61])=[CH:57][N:56]=3)=[CH:53][CH:54]=2)[CH2:25][C:24]([F:62])([F:23])[CH2:28][N:27]1[C:29]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:30])=[O:37]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 66705621Tert-butyl 4,4-difluoro-2-[4-(5-fluoropyridin-2-yl)benzyl]-2-{[(2-hydroxy-4,4-dimethylhexyl)amino]carbonyl}pyrrolidine-1-carboxylate

Product 1

HCID 66705635Tert-butyl 2-{[(4,4-dimethyl-2-oxohexyl)amino]carbonyl}-4,4-difluoro-2-[4-(5-fluoropyridin-2-yl)benzyl]pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (304 mg, 0.72 mmol) was added to an ambient temperature solution of tert-butyl 4,4-difluoro-2-[4-(5-fluoropyridin-2-yl)benzyl]-2-{[(2-hydroxy-4,4-dimethylhexyl)amino]carbonyl}pyrrolidine-1-carboxylate (202 mg, 0.36 mmol) in dichloromethane (5 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}-4,4-difluoro-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-bedbce1ccc43404bbb03cd4d0db8ccb2
Source dataset
uspto-grants-2012_11
Patent number
US08318767B2

Reaction notes

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