Water → HCID 59556992, compound

HRID 1967244Notes

Reaction equation

HRID 1967244 reaction equation
[OH:1][C@@H:2]1[C@H:6]([CH3:7])[NH:5][C:4](=[O:8])[CH2:3]1.N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])(=O)=O.O>C1COCC1>[Si:23]([O:1][C@@H:2]1[C@H:6]([CH3:7])[NH:5][C:4](=[O:8])[CH2:3]1)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 11062347(4S,5S)-4-hydroxy-5-methylpyrrolidin-2-one

Product 1

HCID 59556992HCID 59556992, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (4S,5S)-4-hydroxy-5-methylpyrrolidin-2-one (3.0 g) in THF (50 mL) was cooled to 0° C., 2,6-lutidine (4.55 mL) and tert-butyldimethylsilyl trifluoromethanesulfonate (6.6 mL) were added thereto and, after warming to room temperature, the mixture was stirred at room temperature for 18 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1→1/2) to give the title compound as a colorless solid (yield: 4.54 g, 76%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1→1/2)

Sources & evidence

ORD record
ord-a73c4c857c984afdb606e8acf87f363c
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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