Sodium Azide → HCID 178454124, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of cis-3-((tert-butoxycarbonyl)amino)cyclobutyl methanesulfonate (29 g, 109 mmol) in DMF (100 mL) was added sodium azide (5.68 mL, 162 mmol) portionwise and the mixture stirred at 85° C. for 18 h. After cooling, the reaction mixture was diluted with water (200 mL) and extracted with EtOAc (3×100 mL). The combined organic was washed with water (2×100 mL) and brine, dried over Na2SO4 and evaporated in vacuo to give the desired product tert-butyl(cis-3-azidocyclobutyl)carbamate (22 g, 104 mmol, 95% yield) that was used in the next step without further purification. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 4.68 (br. s., 1 H), 3.87 (br. s., 1 H), 3.44-3.68 (m, 1 H), 2.75 (d, J=6.85 Hz, 2 H), 1.90 (q, J=9.19 Hz, 2 H), 1.44 (s, 10 H).

Provenance & Evidence