m-Chloroperbenzoic acid → HCID 86664649, compound

HRID 1917342Notes

Reaction equation

HRID 1917342 reaction equation
[C:1]([O:5][C:6]([C@@:8]1([CH2:22][CH:23]=[CH2:24])[CH2:12][C:11](=[O:13])[N:10]([C@@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:33])C=1>C(Cl)Cl>[C:1]([O:5][C:6]([C:8]1([CH2:22][CH:23]2[CH2:24][O:33]2)[CH2:12][C:11](=[O:13])[N:10]([C@@H:14]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 67490875(3S)-3-Allyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester

Product 1

HCID 86664649HCID 86664649, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3S)-3-Allyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester (4.9 g, 14.9 mmol) was dissolved in methylene chloride, and mCPBA (10.3 g, 59.5 mmol) was added. The mixture was stirred at room temperature for 15 hours and then heated to reflux for three hours. The solvent was evaporated under reduced pressure, and then the residue was blended with a mixture of ethyl acetate and a saturated sodium thiosulfate solution. The organic layer was washed with saturated sodium bicarbonate water, dried over magnesium sulfate, and filtered, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=4:1→1:1) to give 4.33 g (84%) of the colorless oil title compound as a diastereomer mixture. The diastereomers were used for the next step without separation and purification.

Workup

  1. temperatureheated
  2. temperatureto reflux for three hours
  3. customThe solvent was evaporated under reduced pressure
  4. additionthe residue was blended with a mixture of ethyl acetate
  5. washThe organic layer was washed with saturated sodium bicarbonate water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=4:1→1:1)

Sources & evidence

ORD record
ord-cc4a171acd9349c8b3446cc2beb1737c
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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