Methyl iodide → 2-(3,4-Dichloro-phenyl)-3-(3-methoxy-cyclopentyl)-propionic acid methyl ester

HRID 854802Notes

Reaction equation

HRID 854802 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH:4]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH:8]([OH:11])[CH2:7]1.I[CH3:22]>C(#N)C.C(=O)([O-])[O-].[Ag+2].F[B-](F)(F)F.[Ag+]>[CH3:1][O:2][C:3](=[O:20])[CH:4]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH:8]([O:11][CH3:22])[CH2:7]1

Participants

6

Reactant 2

HCID 6328Methyl iodideHCID 674821392-(3,4-Dichloro-phenyl)-3-(3-hydroxy-cyclopentyl)-propionic acid methyl ester

Product 1

HCID 674821362-(3,4-Dichloro-phenyl)-3-(3-methoxy-cyclopentyl)-propionic acid methyl esterYield 34.1%

Reagents, catalysts & solvents 3

HCID 159722Silver tetrafluoroborateCatalystHCID 178418647HCID 178418647, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of 2-(3,4-dichloro-phenyl)-3-(3-hydroxy-cyclopentyl)-propionic acid methyl ester (prepared as in Example 36, 194.1 mg, 0.61 mmol), silver carbonate (320.6 mg, 1.16 mmol), silver tetrafluoroborate (131.0 mg, 0.67 mmol), and iodomethane (72 μL, 1.16 mmol) in acetonitrile (6.1 mL) was stirred at 25° C. for 48 h. The resulting reaction mixture was then heated under reflux for 24 h. The reaction mixture was then filtered through a pad of celite, and the celite pad was washed well with ethyl acetate. The filtrate was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 10% ethyl acetate/hexanes) afforded 2-(3,4-dichloro-phenyl)-3-(3-methoxy-cyclopentyl)-propionic acid methyl ester (68.8 mg, 34%) as a yellow oil which was used without further purification.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas then heated
  3. temperatureunder reflux for 24 h
  4. filtrationThe reaction mixture was then filtered through a pad of celite
  5. washthe celite pad was washed well with ethyl acetate
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6ec6d9763c6a48539b60fc5fe9e42af5
Source dataset
uspto-grants-2007_08
Patent number
US07259166B2

Reaction notes

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