Water → HCID 59556990, compound

HRID 1967377Notes

Reaction equation

HRID 1967377 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C@@H:13]([CH3:14])[C@H:12]([OH:15])[C:11]([F:17])([F:16])[C:10]2=[O:18])[CH:5]=[CH:6][C:7]=1I.O.[CH3:20][N:21](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C@@H:13]([CH3:14])[C@H:12]([OH:15])[C:11]([F:17])([F:16])[C:10]2=[O:18])[CH:5]=[CH:6][C:7]=1[C:20]#[N:21]

Participants

6

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 59556983HCID 59556983, compound

Product 1

HCID 59556990HCID 59556990, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

To a solution of (4S,5S)-1-(3-chloro-4-iodophenyl)-3,3-difluoro-4-hydroxy-5-methylpyrrolidin-2-one (113 mg) in DMF (3.5 mL) were added zinc cyanide (12 mg) and tetrakis(triphenylphosphine)palladium(0) (34 mg), and the mixture was stirred at 100° C. for 4 hr. Water was added to the reaction mixture, 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=30/1→1/2) to give the title compound as a colorless solid (yield: 75 mg, 90%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=30/1→1/2)

Sources & evidence

ORD record
ord-36acaab37f35428cb4837de2329652f3
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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