Acetic Acid → 2-(4-(2-tert-Butoxycarbonylaminoethylamino)piperidin-1-yl)benzoic acid methyl ester

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Reaction Steps

A solution of 45 (195 mg, 0.836 mmol), 1 (175 mg, 1.09 mmol), and acetic acid (251 mg, 4.19 mmol) in methanol (3 mL)/dichloroethane (1 mL) was treated with sodium cyanoborohydride (55 mg, 0.875 mmol) at room temperature. The resulting mixture was stirred at room temperature (3 h). The solvent was removed in vacuo and the residue dissolved in dichloromethane and sodium carbonate solution. The aqueous layer was extracted with two additional portions of dichloromethane and the combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. PCTLC (SiO2, 4 mm, 1% NH4OEt-10% EtOH-90% CHCl3) afforded the title compound (46).

Provenance & Evidence