Hydroxyamine hydrochloride → Methyl 2-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

Participants

Reaction Steps

Into a flask containing a solution of methyl 2-formyl-1-((2-(trimethylsilyl)-ethoxy)-methyl)-1H-imidazole-4-carboxylate (9 g, 31.6 mmol) in MeOH (200 ml), 50% aqueous NH2OH.HCl solution (2.5 ml) was added and stirred at RT for 3 h. The reaction mixture was concentrated and extracted with EtOAc. The organic layer was concentrated and the resulting residue was dissolved in DCM (200 ml). Pyridine (12 ml) and trifluoroacetic anhydride (18 ml) were added to the above mixture and stirred for 12 h. The reaction mixture was quenched with aqueous NaHCO3 solution and extracted with DCM. The organic layer was concentrated and purified with flash chromatography. Yield 4.1 g. 1H-NMR (400 MHz; DMSO-d6): δ −0.04 (s, 9H), 0.87 (t, 2H), 3.56 (t, 2H), 3.81 (s, 3H), 5.29 (s, 2H), 8.28 (s, 1H).

Provenance & Evidence