Hydroxylamine → tert-butyl N-{5-[amino(hydroxyimino)methyl]-2-fluorobenzyl}-N-methyl-beta-alaninate

Participants

Reaction Steps

Hydroxylamine (50% in water) (513.54 μL; 8.55 mmol; 5 eq.) was added to a solution of tert-butyl N-(5-cyano-2-fluorobenzyl)-N-methyl-beta-alaninate, obtained in step 1 (500 mg; 1.71 mmol; 1 eq.) in EtOH (20 mL) and the resulting mixture was stirred at RT for 24 hours. Solvent was evaporated in vacuo and the resulting oily residue was freeze-dried to afford the title compound as a colourless oil (560 mg; quantitative). 1H NMR (CDCl3) δ 7.74 (dd, J=6.6, 2.2 Hz, 1H), 7.58-7.53 (m, 1H), 7.03 (t, J=9.1 Hz, 1H), 5.10 (s, 2H), 3.59 (s, 2H), 2.69 (t, J=7.0 Hz, 2H), 2.44 (t, J=6.9 Hz, 2H), 2.28 (s, 3H), 1.46 (s, 9H). LC/MS (Method B): 326.2 (M+H)+. HPLC (Method A) Rt 2.18 min (Purity: 86.2%).

Provenance & Evidence