Hydrochloric Acid → 2-[3-(2-Amino-ethyl)-phenoxy]-2-methyl-propionic acid ethyl ester

Participants

Reaction Steps

7.82 g (28.0 mmol) of 2-methyl-2-[3-((E)-2-nitro-vinyl)-phenoxy]-propionic acid ethyl ester was dissolved in 150 ml ethanol; 6.2 ml (39.7 mmol) hydrochloric acid in ethanol and 1.6 g of Pd-charcoal (10%) were added and the reaction mixture was then hydrogenated under 1 atm of H2-pressure during 5 hours. It was subsequently filtered (Celite), the filter cake was washed twice with ethanol and filtrate was evaporated. The residue was then partitioned between crashed ice/Na2CO3-solution/MeCl2 and extracted twice with MeCl2; the organic phases were washed with water, dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (SiO2, MeCl2/MeOH) to give 4.36 g of the title compound as yellow oil.

Provenance & Evidence