Acetic acid, azido-, ethyl ester → ethyl[4-(1-hydroxycyclopentyl)-1H-1,2,3-triazol-1-yl]acetate

Participants

Reaction Steps

Ethyl azidoacetate (2.58 g, 20 mmol) was dissolved in tert-butanol (15 mL), and 1-hydroxycyclopentanecarbonitrile (2.20 g, 20 mmol) was added. A solution of sodium ascorbate (0.792 g, 4 mmol) in water (10 mL) followed by a 0.3 M solution of copper sulfate (0.67 mL) was added to the mixture, and stirring continued at room temperature for a further 48 hours. The solution was evaporated to dryness in vacuo and the residue was dissolved in EtOAc (50 mL), dried (MgSO4), filtered and evaporated in vacuo to afford the title compound as green-yellow crystals in 98% yield, 4.69 g. MS m/z 238 [M−H]−

Provenance & Evidence