HCID 67399199, compound → HCID 67398525, compound

HRID 70626Notes

Reaction equation

HRID 70626 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([O:26][CH3:27])[N:20]=2)=[CH:12][C@@H:13]2[NH:17][C:16](=[O:18])[CH2:15][CH2:14]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([O:26][CH3:27])[N:20]=2)[CH2:12][C@@H:13]2[NH:17][C:16](=[O:18])[CH2:15][CH2:14]2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 67399199HCID 67399199, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67398525HCID 67398525, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5% palladium-activated carbon (30 mg) was added to a solution of (5R)-5-[2-(4-tert-butylphenyl)-2-(5-chloro-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one (E:Z=2:8) (150 mg) in methanol in a hydrogen gas stream, and the mixture was stirred at room temperature for seven hours. The reaction solution was filtered through celite, and the solvent was evaporated under reduced pressure. The resulting residue was purified by NH-silica gel column chromatography (chloroform) and further purified by preparative TLC (chloroform) to give (5R)-5-[2-(4-tert-butylphenyl)-2-(5-chloro-6-methoxypyridin-2-yl)ethyl]pyrrolidin-2-one as a pale brown amorphous (110 mg, 73%).

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. customthe solvent was evaporated under reduced pressure
  3. customThe resulting residue was purified by NH-silica gel column chromatography (chloroform)
  4. customfurther purified by preparative TLC (chloroform)

Sources & evidence

ORD record
ord-e8399a14de354aa1885644b4d3a02fbc
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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