Sodium Azide → HCID 59201472, compound

Participants

Reaction Steps

A solution of (3R)-tert-butyl 3-((2,3-difluorophenyl)(2-(methylsulfonyloxy)ethoxy)methyl)piperidine-1-carboxylate (4.2 g, 9.4 mmol) and solid NaN3 (0.92 g, 14.1 mmol) in anhydrous DMF (30 mL) was heated to 80° C. overnight. The reaction mixture was cooled to rt and diluted with ethyl acetate (80 mL), the organic phase was washed with water (30 mL×3), dried over Na2SO4 and evaporated. The residue was separated on a silica column to give (3R)-tert-butyl 3-((2-azidoethoxy)(2,3-difluorophenyl)methyl)piperidine-1-carboxylate (3.4 g, 92%). 1H NMR (CDCl3, 400 MHz) δ 7.14 (m, 3H), 4.50 (q, 1H), 4.10 (m, 1H), 3.40 (m, 4H), 2.70 (m, 2H), 1.90 (m, 2H), 1.65 (m, 1H), 1.41 (d, 9H).

Provenance & Evidence