ethyl 3-(2-phenylethylamino)propanoate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (4-Methyl-pyridin-2-yl)-acetic acid (1.0 g), carbonyldiimidazole (CDI, 1.07 g) and DIPEA (0.856 g) were added to THF (15 ml) and the light brown suspension was allowed to stir at RT for 1 hour. To the mixture was added 3-phenethylamino-propionic acid ethyl ester (0.898 g) dropwise and the resulting mixture was stirred at 55° over night. The mixture was poured into ice/water and the pH was adjusted to 5.0. The mixture was extracted with ethyl acetate and the organic layer was separated, washed with brine, dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (ethyl acetate/hexanes 2:1) to give the desired product as a light brown liquid (0.462 g). MS (ESI): 355.0 (MH+). the resulting mixture was stirred at 55° over night The mixture was extracted with ethyl acetate the organic layer was separated washed with brine dried over Na2SO4 filtered evaporated The residue was purified by flash chromatography (ethyl acetate/hexanes 2:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (4-Methyl-pyridin-2-yl)-acetic acid (1.0 g), carbonyldiimidazole (CDI, 1.07 g) and DIPEA (0.856 g) were added to THF (15 ml) and the light brown suspension was allowed to stir at RT for 1 hour. To the mixture was added 3-phenethylamino-propionic acid ethyl ester (0.898 g) dropwise and the resulting mixture was stirred at 55° over night. The mixture was poured into ice/water and the pH was adjusted to 5.0. The mixture was extracted with ethyl acetate and the organic layer was separated, washed with brine, dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (ethyl acetate/hexanes 2:1) to give the desired product as a light brown liquid (0.462 g). MS (ESI): 355.0 (MH+). the resulting mixture was stirred at 55° over night The mixture was extracted with ethyl acetate the organic layer was separated washed with brine dried over Na2SO4 filtered evaporated The residue was purified by flash chromatography (ethyl acetate/hexanes 2:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenylethyl amine (10 g) was dissolved in EtOH (50 ml) and then treated with acrylic acid ethyl ester (8.3 g) dropwise under argon at RT. The resulting mixture was allowed to stir over night and was evaporated and dried in vacuo. The residue (18.9 g) was used without further purification. Colorless liquid, MS (ESI): 222.3 (MH+). was evaporated dried in vacuo The residue (18.9 g) was used without further purification