Ethyl (3S)-piperidine-3-carboxylate Chemical Properties

Boiling point:

102-104 °C/7 mmHg(lit.)

Density 

1.043 g/mL at 25 °C

refractive index 

n20/D 1.471

Flash point:

77 °C

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

pka

9.35±0.10(Predicted)

form 

clear liquid

color 

Colorless to Almost colorless

Specific Gravity

1.012

optical activity

-3.4°(C=0.01 g/ml, CHCL3, 20°C, 589nm)

Sensitive 

Light, Air & Moisture Sensitive

CAS DataBase Reference

37675-18-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-41

Safety Statements 

26-36/37/39-39-36

RIDADR 

NA 1993 / PGIII

WGK Germany 

3

HS Code 

29339900

Ethyl (3S)-piperidine-3-carboxylate Usage And Synthesis

Chemical Properties

Colorless liquid

Uses

Reactant for synthesis of:

• DPP-4 inhibitors
• JAK2 inhibitors
• Serotonin and noradrenaline reuptake inhibitors
• Human tryptase inhibitors
• Anti-thrombotic nicecotamides

Reactive for oxidative C-arylation of free (NH)-heterocycles via direct (sp3) C-H bond functionalization

Synthesis

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.

References

[1] Patent: US2004/122018, 2004, A1. Location in patent: Page 208

Ethyl (3S)-piperidine-3-carboxylate(37675-18-6)Related Product Information

• Ethyl nipecotate
• Ethylparaben
• Ethyl formate
• Benzocaine
• Ethyl acetate
• Ethyl cellulose
• Ethanol
• Ethyl acrylate
• Nipecotic acid
• Urethane
• Ethyl 4-piperidinecarboxylate
• RESMETHRIN
• Ethyl (S)-nipecotate L-tartrate
• COCAETHYLENE
• Piperidine
• Ethyl chloroformate
• Diethyl ether
• 1,3-Piperidinedicarboxylic acid, 1-(1,1-dimethylethyl) 3-ethyl ester, (3S)- (9CI)