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

Participants

Reaction Steps

To a solution of 2-formyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carboxylic acid methyl ester (0.11 g, 0.38 mmol) (as prepared in the previous step) in methanol (2 mL) was added a 50% aqueous hydroxylamine solution (30 μL) and the reaction stirred for 3 h at RT and then concentrated. The residue was dissolved in DCM (2 mL), pyridine (0.13 mL), and trifluoroacetic anhydride (0.17 mL, 1.1 mmol) was added and the reaction stirred for 10 h at RT. The reaction was diluted with EtOAc (10 mL) and washed with satd. NaHCO3 (2×10 mL) and the organic layer dried over Na2SO4 and then concentrated. The title compound was eluted from a 10-g SPE cartridge (silica) with 30% EtOAc/hexane to give 0.085 g (76%) of a colorless oil. 1H-NMR (400 MHz, CDCl3): δ 7.99 (s, 1H), 5.50 (s, 2H), 3.92 (s, 3H), 3.58 (m, 2H), 0.94 (m, 214), 0.00 (s, 9H).

Provenance & Evidence