3-Cyclopentyl-2-(4-ethanesulfonyl-phenyl)-acrylic acid ethyl ester → 3-Cyclopentyl-2-(4-ethanesulfonyl-phenyl)-propionic acid ethyl ester

HRID 430281Notes

Reaction equation

HRID 430281 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[C:5]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH2:21][CH3:22])(=[O:20])=[O:19])=[CH:14][CH:13]=1)=[CH:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)[CH3:2].[H][H]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:23])[CH:5]([C:12]1[CH:13]=[CH:14][C:15]([S:18]([CH2:21][CH3:22])(=[O:20])=[O:19])=[CH:16][CH:17]=1)[CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1)[CH3:2]

Participants

5

Reactant 2

HCID 538130643-Cyclopentyl-2-(4-ethanesulfonyl-phenyl)-acrylic acid ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 543970993-Cyclopentyl-2-(4-ethanesulfonyl-phenyl)-propionic acid ethyl esterYield 71.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-cyclopentyl-2-(4-ethanesulfonyl-phenyl)-acrylic acid ethyl ester [4.89 g, 14.53 mmol, (E):(Z)=3:1] in ethanol (36 mL) was slowly treated with 10% palladium on activated carbon (244.5 mg). The reaction mixture was stirred under a positive pressure of hydrogen gas (balloon) at 25° C. and atmospheric pressure for 44 h. The catalyst was then filtered off 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, 70-230 mesh, 3/1 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-ethanesulfonyl-phenyl)-propionic acid ethyl ester (3.50 g, 71%) as a colorless viscous oil: FAB-LRMS m/e calcd for C18H26O4S (M+H)+ integer mass 338, found 339.

Workup

  1. filtrationThe catalyst was then filtered off through a pad of celite
  2. washthe celite pad was washed well with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3116b6db75174fe6bc4ca9d2f6c4f2e1
Source dataset
uspto-grants-2001_11
Patent number
US06320050B1

Reaction notes

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