Dichloromethane → 3-(2-Methoxy-pyridin-4-yl)-propionic acid methyl ester

HRID 474760Notes

Reaction equation

HRID 474760 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([O:12][CH3:13])[CH:7]=1.C(Cl)Cl>[Pd].CCO>[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([O:12][CH3:13])[CH:7]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 677751253-(2-Methoxy-pyridin-4-yl)-acrylic acid methyl ester

Product 1

HCID 142234703-(2-Methoxy-pyridin-4-yl)-propionic acid methyl esterYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 3-(2-methoxy-pyridin-4-yl)-acrylic acid methyl ester (1.3 g, 6.72 mmol, 1 eq) and Pd/C, 10% (357 mg, 0.05 eq, 10%) was stirred in a DCM (15 ml)/absolute EtOH (15 ml) solvent mixture under hydrogen atmosphere for 1 hour at room temperature. Palladium was filtered off over a celite pad, the solvent was evaporated and obtained crude was purified by chromatography on BIOTAGE SP1 purification device using 25 g normal phase silica SNAP column and cyclohexane/EtOAc solvent system (gradient 3-30% of EtOAc in 20 column volumes). Solvent from the gathered fractions of appropriate composition was evaporated and obtained was 3-(2-methoxy-pyridin-4-yl)-propionic acid methyl ester (1.22 g, yield=88.2%, purity=95%) in form of transparent colourless oil. MS: [M+H]+=196.14 1H NMR (300 MHz; CDCl3) δ/ppm 2.63(t, J=7.91 Hz, 2H), 2.90 (t, J=7.91 Hz, 2H), 3.68(s, 3H), 3.92 (s, 3H), 6.57 (s, 1H), 6.72 (dd, J=5.33 Hz, J=1.29 Hz, 1H), 8.06 (d, J=5.33 Hz, 1H)

Workup

  1. filtrationPalladium was filtered off over a celite pad
  2. customthe solvent was evaporated
  3. customobtained crude
  4. customwas purified by chromatography on BIOTAGE SP1 purification device
  5. customSolvent from the gathered fractions of appropriate composition was evaporated
  6. customobtained

Sources & evidence

ORD record
ord-83a297fe30c34276a3700a1011d43b82
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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