Ammonium Chloride → Tert-butyl 4-(2H-tetrazol-5-YL)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of 2.10 g (10.0 mmol) of 1-(t-butoxycarbonyl)-4-cyanopiperidine (from Step A), 1.95 g (30.0 mmol) of sodium azide and 1.60 g (30.0 mmol) of ammonium chloride in 20 mL of DMF was stirred at 100° C. for 20 h. The mixture was cooled and partitioned between 200 mL of CH2Cl2 and 200 mL of 1.0N HCl and the layers were separated. The organic layer was washed with 200 mL of H2O, dried over MgSO4 and concentrated. Flash chromatography on 50 g of silica gel using 4:1 v/v CH2Cl2/EtOAc+1% HOAc, then 2:1 v/v CH2Cl2/EtOAc+1% HOAc as the eluant afforded 1.51 g (60%) of the title compound: 1H NMR (500 MHz) δ1.49 (s, 9H), 1.83-1.89 (m, 2H), 2.13-2.15 (m, 2H), 2.96-3.04 (m, 2H), 3.13-3.36 (m, 1H), 4.14-4.22 (m, 2H).

Provenance & Evidence