tert-butyl N-(1-hydroxy-2-methylpropan-2-yl)oxycarbamate

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-(N-Boc-aminooxy)isobutyric acid ethyl ester (2.35 g, 9.5 mmol) in anhydrous ethyl ether (100 mL) at 0° C. under nitrogen was added 1.0 M lithiumtetrahydroaluminate in tetrahydrofuran (17.1 mL, 17 mmol), and the reaction mixture stirred at 0° C. for 5 hours. The reaction mixture was quenched with water (25 mL) and allowed to warm to room temperature. The suspension was filtered and the residue washed with diethyl ether and layers separated. The organic extract was dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as a white solid (1.94 g, 99%). 1H NMR (CDCl3, 400 MHz) 3.40 (s, 2H), 1.50 (s, 9H), 1.20 (s, 6H). The reaction mixture was quenched with water (25 mL) to warm to room temperature The suspension was filtered the residue washed with diethyl ether and layers separated The organic extract was dried (Na2SO4) filtered concentrated in vacuo