Sodium Azide → HCID 92019678, compound

Participants

Reaction Steps

(+/−)-Trans-benzyl 3-methoxy-4-(tosyloxy)pyrrolidine-1-carboxylate (10.3 g, 25.4 mmol) was added to the soln. of sodium azide (5.78 g, 89 mmol) in water (10 mL) and DMF (60 mL) and heated to 100 deg. Celsius overnight. Diluted with EA/water and stirred. The organic layer dried (Na2SO4) and concentrated to give (+/−)-Cis-benzyl 3-azido-4-methoxypyrrolidine-1-carboxylate (6.3 g, 22.80 mmol, 90% yield). 1H NMR (400 MHz, chloroform-d) δ ppm 7.34-7.43 (5 H, m), 5.13-5.21 (2 H, m), 4.01-4.04 (2 H, m), 3.47 (3 H, s), 3.49-3.69 (4 H, m), Hz), LCMS: M+23=299, Rt=2.15 min.

Provenance & Evidence