Acetic Acid → (S)-tert-butyl 4-((2-hydroxy-2-methyl-1-phenylpropyl)amino)piperidine-1-carboxylate

Participants

Reaction Steps

To a flask charged with boc-4-piperidone (2.412 g, 12.10 mmol, Alfa-Aesar) was added DCM (60.5 mL), acetic acid (0.901 mL, 15.74 mmol), (S)-1-amino-2-methyl-1-phenylpropan-2-ol (2 g, 12.10 mmol, BOC Scientific) and sodium triacetoxyborohydride (3.59 g, 16.95 mmol) respectively. The resulting orange suspension was stirred at room temperature for 3 h. LCMS indicated good conversion to desired product. To the mixture was added saturated NaHCO3 and K2CO3 pellets. The mixture was transferred to a separatory funnel and extracted with DCM (2×). The combined organics were dried with Na2SO4, filtered, and dried under reduced pressure. The material thus obtained was used without further purification.

Provenance & Evidence