[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][C:8]([O:10]C)=[O:9])[CH2:3][CH2:2]1.[CH3:12][C:13]([CH3:15])=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.Cl>[CH:13]([N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][C:8]([OH:10])=[O:9])[CH2:3][CH2:2]1)([CH3:15])[CH3:12]Methyl 4-piperidineacetate (0.6 g, 3.82 mmol) was dissolved in methylene chloride (20 mL), acetone (1 mL), acetic acid (0.26 mL) and sodium triacetoxyborohydride (1.21 g, 5.73 mmol) were added, and the mixture was stirred overnight at room temperature. The solvent was evaporated, and work-up according to a conventional method gave a crude product. The obtained crude product was dissolved in 6 N aqueous hydrogen chloride solution, and the mixture was stirred overnight at 80° C. The solvent was evaporated to give the title compound, which was used for the synthesis of A-22.
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