Triethylamine → Benzyl 4-Hydroxy-1-piperidinecarboxylate

Participants

Reaction Steps

A solution of benzyl chloroformate (35.3 ml, 0.25 moles) in 25 ml of methylene chloride was added dropwise under nitrogen over three hours to a solution of 4-hydroxypiperidine (25 g, 0.25 moles) and triethylamine (34.5 ml, 0.25 moles) in 500 ml of methylene chloride at ice bath temperature. After the addition the reaction was stirred at ice bath temperature for four hours and at room temperature overnight. The reaction was then extracted two times with 1N HCl, dried (MgSO4) and the solvent removed under reduced pressure to give 53.1 g (90%) of the tide compound as a light yellow oil.

Provenance & Evidence