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

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To a solution of (S)-tert-butyl 3-cyclohexyl-1-(ethylamino)-1-oxopropan-2-ylcarbamate (444 mg, 1.49 mmol) in anhydrous toluene at 0° C. was added Red-Al (65%, 1.39 g, 1.36 mL, 4.47 mmol) over 20 min. After the addition, the reaction was allowed to stir at rt 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 (338 mg, 45% over 2 steps). MS ESI +ve m/z 285 (M+H).

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