Acetaldehyde → Phenyl-piperidin-4-yl-methanol

Participants

Reaction Conditions

Reaction Steps

4-benzoyl-piperidine (2.0 g, 10.6 mmol) was added over a solution of 6.8 g of (+)-B-chlorodiisopinocanfeilboran ((+)-DIP-Cl) (21.25 mmol) in dichloromethane (20 mL, dry) cooled down to 3-4° C. After reacting for 72 h, 2.0 mL of acetaldehyde (35.46 mmol) were added and stirred at room temperature for 3 h. 24 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-phenyl4-piperidinemethanol as a white solid with a m.p.=64-66° C. in a 90% yield (84% ee).

Provenance & Evidence