1-Boc-3-cyano-4-oxopyrrolidine Chemical Properties

Melting point:

160-167°C

Boiling point:

360.7±42.0 °C(Predicted)

Density 

1.18±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

powder to crystal

pka

-4.24±0.40(Predicted)

color 

White to Light yellow

LogP

1.11 at 20℃

CAS DataBase Reference

175463-32-8(CAS DataBase Reference)

Safety Information

Risk Statements 

20/21/22-36/37/38

Safety Statements 

9-26-36/37

RIDADR 

UN3439

HazardClass 

6.1

PackingGroup 

III

HS Code 

29339900

1-Boc-3-cyano-4-oxopyrrolidine Usage And Synthesis

Chemical Properties

Light yellow powder

Uses

1-Boc-3-cyano-4-pyrrolidinone is used in the synthesis of new napthyridone antibacterials. Also used in the synthesis of gemifloxacin derivatives containing benzyloxime moiety.

Synthesis

General procedure for the synthesis of 1-Boc-3-cyano-4-pyrrolidinone from ethyl 2-(BOC-(2-cyanoethyl)amino)acetate: 2-(BOC-(2-cyanoethyl)amino)ethyl acetate (16.5 g), an oil, was dissolved in 50 mL of anhydrous ethanol. The solution was slowly added dropwise to 100 mL of anhydrous ethanol solution containing 4 g (0.17 mol) of sodium metal under heated reflux conditions and the reaction was continued at reflux for 1 hour. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was dissolved in 100 mL of water and the aqueous layer was subsequently washed with ethyl acetate (30 mL x 2). The pH of the aqueous layer was adjusted to 4 with 1 mol/L hydrochloric acid and extracted with ethyl acetate. The organic phase was dried with anhydrous magnesium sulfate and filtered. The filtrate was concentrated to about 20 mL, filtered, and the filter cake was washed with a small amount of ethyl acetate and dried to give 16.5 g of white solid 1-Boc-3-cyano-4-pyrrolidinone in 68% yield.

References

[1] Archiv der Pharmazie, 2011, vol. 344, # 8, p. 523 - 529
[2] European Journal of Medicinal Chemistry, 2010, vol. 45, # 11, p. 5498 - 5506
[3] Patent: CN105585518, 2016, A. Location in patent: Paragraph 0024; 0026
[4] Journal of Medicinal Chemistry, 1997, vol. 40, # 22, p. 3584 - 3593
[5] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 24, p. 4399 - 4403

1-Boc-3-cyano-4-oxopyrrolidine(175463-32-8)Related Product Information

• N-Vinyl-2-pyrrolidone
• tert-Butanol
• Sodium L-pyroglutamate
• RESMETHRIN
• tert-Butyl peroxyacetate
• Cyhalofop-butyl
• N-Methyl-2-pyrrolidone
• Pyrrolidine
• Crospovidone
• Butyl acetate
• Ethyl cyanoformate
• 2-Butoxyethanol
• Buprofezin
• Diethylene glycol monobutyl ether
• Polyvinylpyrrolidone
• Methyl 4-cyanobenzoate
• Butyl acrylate
• tert-butyl 3-cyano-1H-indole-1-carboxylate