3-isobutylglutaric anhydride Chemical Properties

Boiling point:

279.3±9.0 °C(Predicted)

Density 

1.054

storage temp. 

Storage temp. 2-8°C

Appearance

Yellow to brown Liquid

Safety Information

HS Code 

2917198090

3-isobutylglutaric anhydride Usage And Synthesis

Uses

3-Isobutylglutaric anhydride is an impurity of Pregabalin (P704800), a ligand for the alpha-2-delta subunit of voltage-gated calcium channels that exhibits anticonvulsant and analgesic activity.

Synthesis

General procedure for the synthesis of 4-isobutyldihydro-2H-pyran-2,6(3H)-dione from 3-isobutylglutaric acid: 3-isobutylglutaric acid (50 g, 266 mmol) was dissolved in propionic anhydride (130 ml), and the reaction mixture was heated and refluxed for 6 h at 140-145 °C. Upon completion of the reaction, propionic acid and unreacted propionic anhydride were removed by distillation under reduced pressure (30-60 °C/15 mm Hg). Subsequently, the product was collected at 100-105 °C/0.5 mm Hg to afford 4-isobutyldihydro-2H-pyran-2,6(3H)-dione as a yellow oil in a yield of 41 g (91% yield) with a GC purity of >98% (HP-1,25 m, 70 kPa, gradient 70-240 °C, 15 °C/min). The structure of the product was confirmed by 1H NMR (CDCl3) and 13C NMR (CDCl3): 1H NMR (CDCl3), δ/ppm: 0.91 (d, 6H, J=6.6Hz), 1.27 (t, 2H, J=7.1Hz), 1.61-1.75 (m, 1H), 2.12-2.50 (m, 3H), 2.85 (dd , 2H, J1=17Hz, J2=4.1Hz); 13C NMR (CDCl3), δ/ppm: 21.86,24.23,25.89,35.43,43.08,166.48.

References

[1] Patent: WO2008/9897, 2008, A1. Location in patent: Page/Page column 8-9
[2] Patent: WO2012/93411, 2012, A2. Location in patent: Page/Page column 18
[3] Journal of the Chemical Society, 1954, p. 516,519
[4] Patent: WO2007/35789, 2007, A1. Location in patent: Page/Page column 30
[5] Patent: WO2009/4643, 2009, A2. Location in patent: Page/Page column 26

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