5-OXO-PYRROLIDINE-2-CARBOXYLIC ACID METHYL ESTER Chemical Properties

Melting point:

21-23℃ lit.

Boiling point:

133-135℃/1mm

Density 

1.204

refractive index 

1.4850

storage temp. 

Inert atmosphere,Room Temperature

form 

Solid

pka

14.65±0.40(Predicted)

color 

Colorless to Brown

InChI

InChI=1S/C6H9NO3/c1-10-6(9)4-2-3-5(8)7-4/h4H,2-3H2,1H3,(H,7,8)/t4-/m0/s1

InChIKey

HQGPKMSGXAUKHT-BYPYZUCNSA-N

SMILES

C(OC)(=O)[C@@H]1CCC(=O)N1

Safety Information

HS Code 

2933790090

5-OXO-PYRROLIDINE-2-CARBOXYLIC ACID METHYL ESTER Usage And Synthesis

Uses

Methyl 5-Oxopyrrolidine-2-carboxylate, a purinoceptor antagonists in humans.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 28, p. 1143, 1991 DOI: 10.1002/jhet.5570280452

Synthesis

Sulfoxide chloride (6.60 mL, 90.6 mmol) was slowly added to a solution of 5-oxopyrrolidine-2-carboxylic acid (9.00 g, 69.7 mmol) in methanol (20 mL) at 0 °C. The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the mixture was concentrated under vacuum. The residue was diluted with deionized water (100 mL) and extracted with ethyl acetate (100 mL). The organic phase was separated and washed sequentially with deionized water (20 mL) and saturated saline (50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give methyl 5-oxopyrrolidine-2-carboxylate (5.60 g, 58% yield) as a colorless liquid. The product did not need further purification and could be used directly in the subsequent reaction. Mass Spectrometry (ESI) m/z [M+H]+: 144.00, retention time: 1.33 min, relative abundance: 68.6%.1H NMR (400 MHz, DMSO-d6) δ 2.04-2.18 (m, 2H), 3.56-3.62 (m, 2H), 3.70 (s, 3H), 4.16-4.22 (m, 1H). 7.97 (s, 1H).

References

[1] Journal of Heterocyclic Chemistry, 1991, vol. 28, # 4, p. 1143 - 1146
[2] Synthesis (Germany), 2016, vol. 48, # 14, p. 2226 - 2244
[3] Journal of the American Chemical Society, 1987, vol. 109, # 25, p. 7925 - 7926
[4] Chemistry - A European Journal, 2005, vol. 11, # 8, p. 2577 - 2590
[5] Patent: EP2098526, 2009, A1. Location in patent: Page/Page column 13

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