Pipecolic Acid → Methyl pipecolinate

Participants

Reaction Steps

A slurry of 26 g (0.20 mole) of pipecolinic acid in 100 ml of methanol is cooled to -10° and 16.7 ml (0.22 mole) of thionyl chloride added over 5 minutes. The slurry is allowed to warm to ambient temperature and stirred overnight whereupon a thick slurry forms. Addition of 300 ml of methanol gives a solution which is evaporated in vacuo. The residue is suspended in 100 ml of methanol, treated with a solution of 10.8 g (0.2 mole) of sodium methoxide in 100 ml of methanol, and diluted with 400 ml of ether. The solid which forms is filtered and the filtrate evaporated and redissolved in ether. Filtration, evaporation and solution are repeated three times and the final residue distilled in vacuo to give 24.6 g (85%) of the above titled ester, bp. 70°-70.5° at 4.0 mm.

Provenance & Evidence