Bromocycloheptane → HCID 69651826, compound

Participants

Reaction Steps

A solution of the product from step b (2.74 g, 11.1 mmol) and cycloheptyl azide (prepared by the reaction of cycloheptyl bromide and sodium azide) (1.54 g, 11.1 mmol) in toluene (14 ml) was heated under reflux for 42 hours. The solvent was removed invacuo and the residue purified by flash column chromatography (hexane:EtOAc 3:1) to yield 5-(adamantan-1-yloxymethyl)-3-cycloheptyl-3H-[1,2,3]triazole-4-carboxylic acid methyl ester (1.53 g, 36%). 1H NMR (CDCl3) 5.27-5.21 (1H, m), 4.73 (2H, s), 3.94 (3H, s), 2.20-2.11 (7H, m), 1.86-1.85 (8H, m), 1.69-1.60 (12H, m). Further eluation gave rise to 5-(adamantan-1-yloxymethyl)-1-cycloheptyl-1H-[1,2,3]triazole-4-carboxylic acid methyl ester (2.00 g, 47%). 1H NMR (CDCl3) 4.93 (2H, s), 4.74-4.65 (1H, m), 3.94 (3H, s), 2.32-2.04 (8H, m), 2.00-1.54 (19H, m).

Provenance & Evidence