Acetaldehyde → Phenyl-piperidin-4-yl-methanol

Participants

Reaction Conditions

Reaction Steps

4-benzoyl-piperidine (7.35 g, 39.05 mmol) was added over a solution of 25 g of (−)-DIP-Cl (78.125 mmol) in dichloromethane (75 mL, dry) cooled down to 0-2° C. After reacting for 72 h, 5.2 mL of acetaldehyde (92.2 mmol) were added and stirred at room temperature for 3 h. 71 mL of an aqueous NaOH (6N) solution, dichloromethane and saturated aqueous NaCl solution were added. The phases were separated and the usual treatment of the organic phase provided (−)-α-phenyl-4-piperidinemethanol as a white solid with a m.p.=48-50° C. in a 85% yield (86% ee).

Provenance & Evidence