3-tert-Butoxycarbonyl-7-chloro-6-chloromethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine → 3-tert-butoxycarbonyl-7-chloro-6-(3H-[1,2,3]triazol-4-ylthiomethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Participants

Reaction Steps

Slurry 1H-[1,2,3]triazole-5-thiol sodium salt (465 mg, 3.78 mmol) in anhydrous DMF (20 mL). Add a solution of 3-tert-butoxycarbonyl-7-chloro-6-chloromethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1.1 g, 3.4 mmol) in anhydrous DMF (10 mL) dropwise over 10 min under nitrogen. Stir at room temperature for 3 h. Quench by addition of saturated NH4Cl (100 mL). Extract with EtOAc (3×50 mL) and dry the combined organic extracts with water and brine. Dry the organic phase over Na2SO4, filter and concentrate in vacuo to obtain 3-tert-butoxycarbonyl-7-chloro-6-(3H-[1,2,3]triazol-4-ylthiomethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1.2 g, 90%) as a yellow oil suitable for use without further purification.

Provenance & Evidence