1-(Azidomethyl)-4-methoxybenzene → HCID 18697745, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 4-(4-t-butoxycarbonylamino-2-nitrophenyl)-4-hydroxy-2-butynoate (693 mg, 1.90 mmol) prepared in the step (a) and 4-methoxybenzylazide (776 mg, 4.76 mmol) were dissolved in toluene (30 ml), and the solution was stirred at 100° C. overnight. The solvent was removed under reduced pressure, and the residue was purified by chromatography on silica gel (n-hexane:ethyl acetate=1:1) to give a 1:1 mixture (1.33 g) of ethyl 4-((4-t-butoxycarbonylamino-2-nitrophenyl)hydroxymethyl)-1-(4-methoxybenzyl)-1,2,3-triazole-5-carboxylate and ethyl 5-((4-t-butoxycarbonylamino-2-nitrophenyl)hydroxymethyl)-1-(4-methoxybenzyl)-1,2,3-triazole-4-carboxylate. This mixture (1.33 g) was dissolved in methylene chloride (30 ml), active manganese dioxide (3.5 g) was added to the solution, and the mixture was stirred for 30 min. Manganese dioxide was filtered off through Celite, the filtrate was concentrated under reduced pressure, and the residue was purified by chromatography on silica gel (n-hexane:ethyl acetate=2:1) to give a 1:1 mixture (872 mg, 87%) of ethyl 4-(4-t-butoxycarbonylamino-2-nitrobenzoyl)-1-(4-methoxybenzyl)-1,2,3-triazole-5-carboxylate and ethyl 5-(4-t-butoxycarbonylamino-2-nitrobenzoyl)-1-(4-methoxybenzyl)-1,2,3-triazole-4-carboxylate.

Provenance & Evidence