[C:1]([O:5][C:6]([NH:8][C@H:9]([C:12](OC)=[O:13])[CH2:10][Cl:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[BH4-].C1COCC1.C([O-])(O)=O.[Na+]>C(O)C.C(Cl)Cl.CC(C)=O>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([CH2:12][OH:13])[CH2:10][Cl:11])([CH3:4])([CH3:2])[CH3:3]A solution of methyl N-(tert-butoxycarbonyl)-3-chloro-L-alaninate (56, 2.13 g, 9.0 mmol) in ethanol (41 ml) stirred at 0° C. under N2 atmosphere was treated with a 2M solution of LiBH4 in THF (5 mL, 10 mmol) (slow addition). The reaction mixture was slowly warmed up to room temperature and further stirred for 4 h, cooled to 0° C., treated with saturated NaHCO3 (5 mL) followed by acetone (5 mL), stirred for 10 minutes, diluted with DCM and washed with brine, dried over MgSO4 filtered and concentrated to afford 1.94 (100% yield) of title compound as a white solid. MS: m/z=232.0 (MNa+).
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