Cyclobutanone → 1-Cyclobutylpiperidin-4-ol

Participants

Reaction Steps

A solution of 4-piperidinol (80 g, 0.792 moles) and cyclobutanone (67.2 g, 0.96 moles) in ethylene dichloride (1 L) was treated with sodium triacetoxyborohydride (251.1 g, 1.184 moles) portion wise and the mixture was stirred at room temperature for 5 hours. The reaction mixture was quenched in chilled water (1 L) and the resulting mass was basified with lye solution. The layers were separated, and the aqueous layer was extracted with dichloromethane (2×500 mL). The combined organic layers were washed with water, dried over sodium sulfate and concentrated to afford the title compound 100 g (Yield: 81.46%).

Provenance & Evidence