(S)-2-(Boc-amino)-3-cyclohexyl-N-methoxy-N-methylpropanamide → (S)-tert-butyl 1-cyclohexyl-3-oxopentan-2-ylcarbamate

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To a solution of (S)-tert-butyl 3-cyclohexyl-1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate (5.23 g, 16.66 mmol) in anhydrous toluene (80 mL) at −20° C. was added EtMgBr (3 M in Et2O, 16.7 mL, 49.97 mmol) slowly. The reaction was allowed to warm to 0° C., and stirred at this temperature for 2 h. The reaction was quenched with 1 M HCl at 0° C. and extracted with EtOAc. The organic phase was washed with sat. aq. NaHCO3, brine, concentrated to give (S)-tert-butyl 1-cyclohexyl-3-oxopentan-2-ylcarbamate. The product was used in the next step without further purification. MS ESI +ve m/z 306 (M+Na).

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