methyl 3-oxocyclopentane-1-carboxylate Chemical Properties

Boiling point:

130-140℃ (10 Torr)

Density 

1.157±0.06 g/cm3(Predicted)

refractive index 

1.4565 (589.3 nm 23℃)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

liquid

color 

light yellow

InChI

InChI=1S/C7H10O3/c1-10-7(9)5-2-3-6(8)4-5/h5H,2-4H2,1H3

InChIKey

KTGCFXSELRVRFH-UHFFFAOYSA-N

SMILES

C1(C(OC)=O)CCC(=O)C1

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-41-52

Safety Statements 

26-39

RIDADR 

UN 3082 9 / PGIII

WGK Germany 

3

HazardClass 

9

PackingGroup 

Ⅲ

HS Code 

2918300090

methyl 3-oxocyclopentane-1-carboxylate Usage And Synthesis

Uses

3-Oxocyclopentanecarboxylic acid methyl ester can be used as a pharmaceutical synthesis intermediate and can be used to synthesize 3-hydroxycyclopentanecarboxylate.

Uses

3-Oxocyclopentanecarboxylic acid methyl ester can be used as a pharmaceutical synthesis intermediate. It can be prepared from 3-oxocyclopentanecarboxylic acid as a raw material and can be used to synthesize 3-hydroxycyclopentanecarboxylic acid ester. Furthermore, it can be used to synthesize a series of heterocyclic compounds with glutaminase inhibitory activity.

Synthesis Reference(s)

Journal of the American Chemical Society, 99, p. 5508, 1977 DOI: 10.1021/ja00458a060

Synthesis

General procedure for the synthesis of methyl 3-oxocyclopentanecarboxylate from methanol and 3-oxo-1-cyclopentanecarboxylic acid: 3-oxocyclopentane-1-carboxylic acid (10.0 g, 78.13 mmol, 1.0 eq.) was dissolved in methanol (100 ml) and the solution was cooled to 0 °C. Subsequently, concentrated sulfuric acid (2 mL) was slowly added and the reaction mixture was heated to 80 °C and maintained for 6 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the complete consumption of the feedstock, the solvent was removed by evaporation under reduced pressure. The crude product obtained was quenched with water (100 mL) and subsequently extracted with ethyl acetate (2 x 100 mL). The organic phases were combined and washed sequentially with saturated sodium bicarbonate solution (1 x 100 mL) and distilled water (1 x 100 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the title product methyl 3-oxocyclopentanecarboxylate as a colorless liquid (10.0 g, 91.0% yield). The product was analyzed by LC-MS showing a UV inactive compound with a mass spectrometry calculated value of [M+H]+ of 142.06 and a measured value of [M+H2O]+ of 159.96.1H NMR (400 MHz, CDCl3) data were as follows: δ 3.73 (s, 3H), 3.17-3.09 (m, 1H), 2.55-2.24 (m, 4H). 2.21-2.04 (m, 2H).

References

[1] Patent: WO2017/27582, 2017, A1. Location in patent: Page/Page column 77
[2] Patent: CN107474024, 2017, A. Location in patent: Paragraph 0408; 0409; 0410; 0411
[3] Patent: WO2003/93231, 2003, A2. Location in patent: Page/Page column 50
[4] Patent: WO2013/170030, 2013, A1. Location in patent: Page/Page column 165-166
[5] Patent: WO2013/28474, 2013, A1. Location in patent: Page/Page column 96

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