Sodium Azide → (3S,4S)-benzyl 3-azido-4-methylpyrrolidine-1-carboxylate

Participants

Reaction Steps

(+/−)-(trans)-benzyl 3-methyl-4-(tosyloxy)pyrrolidine-1-carboxylate (5.00 g, 12.84 mmol) and sodium azide (2.087 g, 32.1 mmol) in DMF (10 mL) was heated under argon at 85° C. for 18 h. The resulting mixture was cooled and diluted with EtOAc and sat. sodium bicarbonate, washed with water, brine, dried over magnesium sulfate, filtered and concentrated to give a tan oil which was purified via preparative chromatography using Hexanes/EtOAc mixtures as the eluant and 40 g silica cartridge. Fractions containing the major product were combined and concentrated to afford the title compound as a near colorless oil (2.01 g, 7.72 mmol, 60%). HPLC (method B) retention time=3.30 min. LCMS (m+Na)=283.2. 1H NMR (400 MHz, CHLOROFORM-d) δ 7.41-7.30 (m, 5H), 5.15 (d, J=6.2 Hz, 2H), 4.00 (t, J=4.3 Hz, 1H), 3.76-3.55 (m, 3H), 3.16-3.02 (m, 1H), 2.47-2.30 (m, 1H), 1.13 (t, J=7.0 Hz, 3H).

Provenance & Evidence