Nitric Acid → (2r)-1-(Nitrooxy)but-2-ylamine nitric acid salt

(2R)-Aminobutan-1-ol (1.01 g, 11.3 mmol) was dissolved in anhydrous acetonitrile (50 mL) and the solution was cooled using an ice bath. To the solution, fuming nitric acid (0.5 mL) was added. A mixture of acetic anhydride (8.3 mL, 90 mmol) and fuming nitric acid (2.3 mL, 57 mmol) were cooled in an ice bath and then added slowly to the aminobutan-1-ol reaction mixture and stirred for 1 hour. Solvent was removed under reduced pressure and the residue obtained was dried overnight under high vacuum to yield the title compound (2.07 g, 10.5 mmol, 93% yield) as a light green solid. 1H NMR (300 MHz, CDCl3) δ 8.22 (s, 2H), 4.75 (dd, J=11.9 and 2.7 Hz, 1H), 4.60-4.53 (m, 1H), 3.46 (s, 1H), 1.61 (m, 2H), 0.92 (t, J=7.4 Hz, 3H). 13C NMR (CDCl3, 75.45 MHz) δ 72.1, 49.7, 22.5, 9.5. LRMS (APIMS) m/z 135 (M−HNO3+H)+.