Water → tert-Butyl(2S,3S)-3-hydroxy-2,3-dimethyl-5-oxo-pyrrolidine-1-carboxylate

HRID 1967264Notes

Reaction equation

HRID 1967264 reaction equation
[OH:1][C@@:2]1([CH3:15])[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:3]1[CH3:14].O.I([O-])(=O)(=O)=[O:18].[Na+]>C(OCC)(=O)C.O.[Ru](=O)=O>[OH:1][C@@:2]1([CH3:15])[CH2:6][C:5](=[O:18])[N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:3]1[CH3:14]

Participants

6

Reactant 3

HCID 962WaterHCID 11622622tert-butyl (2S,3S)-3-hydroxy-2,3-dimethylpyrrolidine-1-carboxylateHCID 23667635Sodium periodate

Product 1

HCID 59556959tert-Butyl(2S,3S)-3-hydroxy-2,3-dimethyl-5-oxo-pyrrolidine-1-carboxylateYield 34.2%

Reagents, catalysts & solvents 2

HCID 16211523Ruthenium dioxide hydrateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl (2S,3S)-3-hydroxy-2,3-dimethylpyrrolidine-1-carboxylate (3.05 g) in ethyl acetate (45 mL) were successively added water (68 mL), ruthenium dioxide monohydrate (566 mg) and sodium periodate (4.57 g) at room temperature. The mixture was stirred at room temperature for 40 hr, the organic layer and the aqueous layer were separated, and the aqueous layer was extracted with ethyl acetate. The obtained organic layers were mixed, isopropanol (0.7 mL) was added, and the mixture was stirred at room temperature for 5 min. The reaction solution was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/10→4/10) to give the title compound as a white powder (yield: 1.11 g, 34%).

Workup

  1. customat room temperature
  2. customthe organic layer and the aqueous layer were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. additionThe obtained organic layers were mixed
  5. additionisopropanol (0.7 mL) was added
  6. stirringthe mixture was stirred at room temperature for 5 min
  7. dry with materialThe reaction solution was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/10→4/10)

Sources & evidence

ORD record
ord-64168ad7f9014fc19ea801cc030c9ad0
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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