Benzeneacetamide → alpha-Methyl-4-methoxyphenylalanine amide

Participants

Reaction Steps

Method B, Transfer hydrogenolysis: Amine 3 (500 mg, 1.47 mmol, 1 eq) was dissolved in i-PrOH (5 mL) under Argon. 10% Pd/C (200 mg, 56% moisture content, 18 wt %) and ammonium formate (601 mg, 9.56 mmol, 6.5 eq.) were added. The mixture was stirred at reflux temperature for 1 h. The mixture was filtered through Celite, the filter pad was washed with EtOH (10 mL) and the filtrates were concentrated to provide 480 mg of a 1:1 mixture of desired compound (293 mg, 96%) and phenylacetamide as a white solid. 1H NMR (DMSO, 400 MHz) 1.14 (s, 3H); 2.10 (bs, 2H); 2.50 (d, J=13.1 Hz, 1H); 2.95 (d, J=13.1 Hz, 1H); 3.69 (s, 3H); 6.80 (d, J=8.5 Hz, 2H); 6.81 (bs, 1H); 6.90 (bs, 1H); 7.09 (d, J=8.5 Hz, 2H). (Phenylacetamide 3.34 (s, 2H); 7.15-7.28 (m, 6H); 7.42 (bs, 1H).). HPLC/MS 4 tR=1.96 min. MS (ESI (+)) m/z=164.2 (M-CONH2). (Phenylacetamide tR=1.76 min. MS (ESI (+)) m/z=136.2 (M+1)).

Provenance & Evidence