[CH:1]1([CH2:7][C@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C@H:9]2[CH2:11][O:10]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N-:20]=[N+:21]=[N-:22].[Na+].[Cl-].[NH4+]>CO>[C:15]([O:14][C:13]([NH:12][C@@H:8]([CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C@H:9]([OH:10])[CH2:11][N:20]=[N+:21]=[N-:22])=[O:19])([CH3:18])([CH3:17])[CH3:16]tert-Butyl (S)-2-cyclohexyl-1-((S)-oxiran-2-yl)ethylcarbamate (492 mg, 1.82 mmol), sodium azide (600 mg, 9.2 mmol), and ammonium chloride (540 mg, 10 mmol) were dissolved in MeOH (26 mL). The reaction was heated to 70° C. for 15 h. The solution was cooled to rt and quenched with water (80 mL). The solution was extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over MgSO4, and the solvent was removed. The crude (2R,3S)-3-amino-1-azido-4-cyclohexylbutan-2-ol (524 mg) was used without further purification.
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