Tert-butyl 4-azido-3,3-difluoropyrrolidine-1-carboxylate → Tert-butyl 4-amino-3,3-difluoropyrrolidine-1-carboxylate

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Reaction Steps

A solution of tert-butyl 4-azido-3,3-difluoropyrrolidine-1-carboxylate (3.01 g, 12.1 mmol) in ethanol (300 mL) was degassed with nitrogen and 20% Pd/C (300 mg) was added. The resulting mixture was stirred under hydrogen atmosphere (balloon) for 16 hr. The catalyst was removed by filtration. The filtrate was evaporated to give the title product as an oil (2.63 g, 98% yield, >85% purity). 1H NMR (400 MHz, chloroform-d) δ ppm 3.73-3.87 (m, 2 H) 3.69 (d, J=10.64 Hz, 1 H) 3.50-3.62 (m, 1 H) 3.13 (d, J=6.85 Hz, 1 H) 1.45-1.48 (m, 9 H). 19F NMR (376 MHz, chloroform-d) δ ppm −115.05-−110.78 (m, 1F) −120.95-−117.90 (m, 1 F). m/z (APCI+) for C9H16F2N2O2 123 (M+H)+.

Provenance & Evidence