1-BENZYL-5-OXO-PYRROLIDINE-3-CARBOXYLIC ACID Chemical Properties

Melting point:

142.0 to 146.0 °C

Boiling point:

471.3±45.0 °C(Predicted)

Density 

1.314±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

4.51±0.20(Predicted)

color 

White to Almost white

CAS DataBase Reference

5733-86-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

RTECS 

UY0686500

HazardClass 

IRRITANT

HS Code 

2933790090

1-BENZYL-5-OXO-PYRROLIDINE-3-CARBOXYLIC ACID Usage And Synthesis

Synthesis

Methyl 1-benzyl-5-oxo-3-pyrrolidinecarboxylate (2.00 g, 8.57 mmol) was used as a raw material and dissolved in a mixed solvent of methanol (10 mL) and tetrahydrofuran (10 mL). Subsequently, 2 N aqueous lithium hydroxide (8.6 mL) was added to this solution. The reaction mixture was heated to reflux for 20 minutes. Upon completion of the reaction, the reaction solution was cooled in an ice bath, adjusted to acidity with aqueous potassium bisulfate, and then extracted with ethyl acetate. The organic layers were combined, concentrated and purified by repurification (ethyl acetate/hexane) and dried to give 1-benzyl-5-oxo-3-pyrrolidinecarboxylic acid (1.83 g, 97% yield).1H-NMR (DMSO-d6) δ: 2.56 (2H, m), 3.80 (1H, m), 3.15 (2H, m), 3.25 (2H, m), 4.36 (2H , q, J = 8.6 Hz), 7.27 (5H, m), 12.61 (1H, s).

References

[1] Patent: EP1403255, 2004, A1. Location in patent: Page 78
[2] Journal of Medicinal Chemistry, 1997, vol. 40, # 15, p. 2374 - 2385
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 377 - 379
[4] European Journal of Organic Chemistry, 2005, # 4, p. 673 - 682
[5] Patent: WO2006/123725, 2006, A1. Location in patent: Page/Page column 64-65

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