3-CYANO-4-OXO-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Chemical Properties

Melting point:

97-99 °C

Boiling point:

375.1±42.0 °C(Predicted)

Density 

1.15±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

-3.72±0.40(Predicted)

color 

Pale Yellow

3-CYANO-4-OXO-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Usage And Synthesis

Uses

3-Cyano-4-oxo-piperidine-1-carboxylic Acid tert-Butyl Ester is a useful research reagent for organic synthesis and other chemical processes.

Synthesis

The general procedure for the synthesis of N-Boc-cyano-piperidin-4-one from ethyl 3-((tert-butoxycarbonyl)(2-cyanoethyl)amino)propionate was as follows: ethyl 3-((tert-butoxycarbonyl)(2-cyanoethyl)amino)propionate (17.3 g, 64.0 mmol) was dissolved in 200 mL of toluene and 60% sodium hydride (3.84 g, 96.0 mmol). The reaction mixture was heated to reflux and maintained for 3 hours. Upon completion of the reaction, it was cooled to room temperature, diluted with 200 mL of water, and the pH was subsequently adjusted to 3 with 1 N hydrochloric acid solution.The aqueous phase was extracted with ethyl acetate (200 mL x 3). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether as eluent to afford 7.8 g (51.6% yield) of tert-butyl 3-cyano-4-oxopiperidine-1-carboxylate as a white solid.1H NMR (400 MHz, DMSO-d6) δ 10.87 (s, 1H), 3.89 (s, 2H), 3.46 (t, J=5.8Hz. 2H), 2.28 (t, J=5.8Hz, 2H).

References

[1] Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9162 - 9183
[2] Patent: US2015/5277, 2015, A1. Location in patent: Paragraph 0208; 0209
[3] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 17, p. 5195 - 5198
[4] Molecules, 2011, vol. 16, # 3, p. 2626 - 2635
[5] Patent: WO2016/86200, 2016, A1. Location in patent: Page/Page column 139; 140; 519; 520

3-CYANO-4-OXO-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(914988-10-6)Related Product Information

• tert-butyl 4-mercaptopiperidine-1-carboxylate
• 1-Piperidinecarboxylicacid,4-hydroxy-2-methyl-,1,1-dimethylethylester,(2S,4R)-(9CI)
• cis-tert-butyl 3-fluoro-4-hydroxypiperidine-1-carboxylate
• 1-Piperidinecarboxylicacid,4-hydroxy-2-methyl-,1,1-dimethylethylester,(2S,4S)-(9CI)
• tert-butyl (3S,4R)-4-aMino-3-fluoropiperidine-1-carboxylate
• 1-BOC-3-METHYL-PIPERIDIN-4-ONE
• 3-CYANO-4-PIPERIDONE
• 3-CYANO-4-OXO-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• N-Boc-3-Cyanopiperidine