Dichloromethane → benzyl 3-(1H-tetrazol-5-yl)pyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of 1.8 g (7.8 mmol) of (R/S)-1-benzyloxycarbonyl-3-cyano pyrrolidine (from Step A), 1.5 g (23 mmol) of sodium azide and 1.25 g (23 mmol) of ammonium chloride in 70 mL of DMF was stirred at 105° C. overnight. After cooling to rt, the reaction was poured into 150 mL of CH2Cl2 and washed with 150 mL of 1N HCl and 2×150 mL of H2O. The organic phase was dried over MgSO4 and concentrated. The residue was purified on a 40M Biotage column using 80:20:1 v/v/v CH2Cl2/EtOAc/HOAc as the eluant to afford 670 mg (31%) of the title compound: RF: 0.23 (80:20:1 v/v/v CH2Cl2/EtOAc/HOAc); 1H-NMR (500 MHz) δ 2.29, 2.48 (2m, 2H), 3.54-4.03 (m, 5H), 5.14-5.24 (m, 2H), 7.30-7.37 (m, 5H), 10.43 (br, 1H).

Provenance & Evidence