N-Iodosuccinimide → HCID 59556983, compound

HRID 1967289Notes

Reaction equation

HRID 1967289 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C@@H:12]([CH3:13])[C@H:11]([OH:14])[C:10]([F:16])([F:15])[C:9]2=[O:17])[CH:5]=[CH:6][CH:7]=1.[I:18]N1C(=O)CCC1=O>C(O)(=O)C.S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C@@H:12]([CH3:13])[C@H:11]([OH:14])[C:10]([F:15])([F:16])[C:9]2=[O:17])[CH:5]=[CH:6][C:7]=1[I:18]

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 57577517HCID 57577517, compound

Product 1

HCID 59556983HCID 59556983, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of (4S,5S)-1-(3-chlorophenyl)-3,3-difluoro-4-hydroxy-5-methylpyrrolidin-2-one (110.5 mg) and N-iodosuccinimide (130 mg) in acetic acid (3 mL) was added dropwise conc. sulfuric acid (3 drops), and the mixture was stirred at room temperature for 18 hr. The reaction mixture was concentrated, water was added and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→1/2) to give the title compound as a pale-yellow oil (yield: 113 mg, 69%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→1/2)

Sources & evidence

ORD record
ord-3f61306308314c309c7cc2487079bfe1
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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