The general procedure for the synthesis of ethyl (S)-3-piperidinecarboxylate from the compound (CAS:183316-65-6) was as follows: 20.0 g of ethyl piperidinate (70.16 g, 0.446 mmol) and D-tartaric acid (67 g, 1.0 eq.) were dissolved in preheated to 95% ethanol (350 mL). The resulting solution was cooled to room temperature and then filtered and the crystals were washed with pre-cooled 95% ethanol. Subsequently, the crystals were recrystallized in 95% ethanol (550 mL) to give tartrate (38.5 g, 56% yield). The resulting tartrate (38.5 g) was dissolved in water (300 mL), cooled to 0 °C and neutralized with 3M NaOH solution. The neutralized solution was extracted with dichloromethane (5 x 100 mL), the organic phases were combined and dried with anhydrous sodium sulfate, and finally concentrated under reduced pressure to give a clarified oily product (19.0 g, 89% yield). Mass spectrometry (CIMS) analysis showed MH+ = 158.
