3-Pyridine aldoxime → HCID 23509808, compound

HRID 1882877Notes

Reaction equation

HRID 1882877 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[N:8][OH:9])[CH:2]=1.[CH2:10]([N:13]1[CH2:17][CH2:16][CH2:15][C:14]1=[O:18])[C:11]#[CH:12]>C(Cl)(Cl)Cl.CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:12]=[C:11]([CH2:10][N:13]3[CH2:17][CH2:16][CH2:15][C:14]3=[O:18])[O:9][N:8]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 6943-Pyridine aldoximeHCID 124643131-(Prop-2-yn-1-yl)pyrrolidin-2-one

Product 1

HCID 23509808HCID 23509808, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

The desired compound was prepared by the method of Example 8 from 500 mg (4.09 mmol) of 3-pyridine aldoxime and 1.0 g (2 equivalents) of 1-propargyl pyrrolidin-2-one prepared in Example 7, and purified by separation with silica gel column chromatography using ethyl acetate and then chloroform/methanol (30:1) to obtain 352.2 mg (35.4% yield) of 1-(3-pyridin-3-yl-isoxazol-5-yl-methyl)-pyrrolidin-2-one.

Workup

  1. custompurified by separation with silica gel column chromatography

Sources & evidence

ORD record
ord-1f8b9e7d113343a6a18caec67aba3f20
Source dataset
uspto-grants-2004_07
Patent number
US06759419B2

Reaction notes

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