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

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Reaction Steps

(3S,4R)-Benzyl 3-ethyl-4-(tosyloxy)pyrrolidine-1-carboxylate (21.25 g, 52.7 mmol) in DMF (50 mL) was added to a solution of sodium azide (8.56 g, 132 mmol) in DMF (50 mL) and water (30 mL) and heated to a bath temp. of 100° C. overnight. The reaction mixture was diluted with ethyl acetate/water and stirred. The organic layer was washed with water, dried (Na2SO4) and concentrated to give (3S,4S)-benzyl 3-azido-4-ethylpyrrolidine-1-carboxylate (14.5 g, 52.9 mmol, 100% yield). 1H NMR (400 MHz, chloroform-d) δ ppm 7.34-7.41 (5H, m), 5.13-5.21 (2H, m), 4.08-4.11 (1H, m), LCMS: M+23=299, t=2.15 min.

Provenance & Evidence