Red-Al → (S)-tert-butyl 1-cyclohexyl-3-(ethylamino)propan-2-ylcarbamate

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(S)-tert-butyl 1-amino-3-cyclohexyl-2-methyl-1-oxopropan-2-ylcarbamate To a solution of (S)-tert-butyl 1-amino-3-cyclohexyl-2-methyl-1-oxopropan-2-ylcarbamate (811 mg, 2.85 mmol) in anhydrous toluene (15 mL) at 0° C. was added Red-Al (65%, 2.66 g, 2.6 mL, 8.55 mmol) within 20 min. After the addition, the reaction was allowed to be stirred at room temperature overnight. The reaction was cooled to 0° C. and quenched with Na2SO4.10H2O. The resulting mixture was stirred for 2-3 h, filtered through Celite, and washed with THF (200 mL). The filtrate was dried and concentrated to give crude product (S)-tert-butyl 1-cyclohexyl-3-(ethylamino)propan-2-ylcarbamate (860 mg). MS ESI +ve m/z 271 (M+H).

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