HCID 58452568, compound → (5R)-5-[(Z)-2-(5-chloro-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one

HRID 70537Notes

Reaction equation

HRID 70537 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:10]#[C:11][C@@H:12]2[NH:16][C:15](=[O:17])[CH2:14][CH2:13]2)=[N:6][C:7]=1[O:8][CH3:9].[H][H]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:10]=[CH:11]\[C@@H:12]2[NH:16][C:15](=[O:17])[CH2:14][CH2:13]2)=[N:6][C:7]=1[O:8][CH3:9]

Participants

5

Reactant 2

HCID 58452568HCID 58452568, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58452452(5R)-5-[(Z)-2-(5-chloro-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-oneYield 71%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 887MethanolSolvent

Procedure

Lindlar catalyst (50 mg) was added to a solution of (5R)-5-[(5-chloro-6-methoxypyridin-2-yl)ethynyl]pyrrolidin-2-one (232 mg) in methanol (5 mL), and the mixture was stirred at room temperature for eight hours in a hydrogen atmosphere. The reaction solution was filtered through celite, and then the solvent was evaporated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→0:1) to give the title compound as a colorless oil (166 mg, 71%).

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. customthe solvent was evaporated
  3. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→0:1)

Sources & evidence

ORD record
ord-fc4f2b1b2a4449ab81dfb631ef6fa8cb
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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