Benzyl [(1S)-1-(4-methoxyphenyl)ethyl]carbamate → (S)-1-(4-Methoxyphenyl)ethylamine

Participants

Reaction Steps

A solution of the above (29) (42.8 g) in methanol (300 mL) was hydrogenated over 5% Pd on carbon (~2 g) at 50 psi H2 for 4 h in a Parr shaker. The product (30) was obtained after filtration of the catalyst through Celite®, rinsing with fresh methanol and evaporation (22.9 g, 100%). GC RT 4.68 min (HP 530 mμ×20 m methylsilicone column, He carrier flow rate 20 mL/min, 100° C. isothermal); 1H NMR (CDCl3) δ1.37 (3H, d, J=7 Hz), 2.25(2H, br s), 2.78(3H, s), 4.08(1H, q), 7.15(4H, q).

Provenance & Evidence