[H-].[H-].[H-].[H-].[Li+].[Al+3].CON(C)[C:10]([CH:12]1[CH2:17][CH2:16][CH2:15][CH:14]([N:18]([CH3:26])[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:13]1)=[O:11]>CCOCC>[CH:10]([CH:12]1[CH2:17][CH2:16][CH2:15][CH:14]([N:18]([CH3:26])[C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:13]1)=[O:11]To a cold (0° C.) suspension of LiAlH4 (380 mg, 9.9 mmol) in Et2O (40 mL) was added dropwise a solution of tert-butyl N-[3-(N-methoxy-N-methylcarbamoyl)cyclo-hexyl]-N-methylcarbamate (2.38 g, 7.92 mmol) in Et2O (40 mL) over 10 min. The reaction mixture was stirred at 0° C. for 0.5 hr, and quenched with 1N KHSO4 (100 mL). The organic phase was separated, dried over MgSO4 and evaporated to give tert-butyl 3-formylcyclohexyl(methyl)carbamate as a colorless oil, which was used for next step without purification (1.66 g, yield;87%).
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