(S)-N-methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide → tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamate

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To a solution of LiAlH4 (0.356 g, 9.38 mmol) in Et2O (20 mL) at 0° C. was added dropwise a solution of N2-{[(1,1-dimethylethyl)oxy]carbonyl}-N1-methyl-N1-(methyloxy)-L-leucinamide (2.34 g, 8.53 mmol) in Et2O (15 mL). The reaction mixture was stirred for 30 min at 0° C. and quenched with EtOAc (6 mL) followed by 5% aq. potassium bisulfate (6 mL). The reaction mixture was washed with 1 M aq. HCl (2×10 mL), saturated aq. NaHCO3 (2×10 mL), and brine (10 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to afford the title compound as a clear, colorless oil.

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