TERT-BUTYL 2,4-DIOXOPIPERIDINE-1-CARBOXYLATE Chemical Properties

Boiling point:

373.8±35.0 °C(Predicted)

Density 

1.199

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

10.67±0.20(Predicted)

form 

powder

color 

Yellow

InChI

InChI=1S/C10H15NO4/c1-10(2,3)15-9(14)11-5-4-7(12)6-8(11)13/h4-6H2,1-3H3

InChIKey

SLCAHLSQXDNQSF-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCC(=O)CC1=O

Safety Information

Risk Statements 

20/21/22

Safety Statements 

23-24/25

WGK Germany 

3

HS Code 

29337900

TERT-BUTYL 2,4-DIOXOPIPERIDINE-1-CARBOXYLATE Usage And Synthesis

Chemical Properties

White powder

Uses

tert-Butyl 2,4-Dioxocyclohexanecarboxylate is a reactant in the synthesis of phenoxymethyl-dihydrothiazolopyridone derivatives as selective positive allosteric modulators (PAMs) of the metabotropic glutamate 5 (mGlu5) receptor.

Synthesis

Step ii: Synthesis of tert-butyl 2,4-dioxopiperidine-1-carboxylate To a 250 mL round-bottomed flask was added 3-((tert-butoxycarbonyl)amino)propanoic acid (4 g, 0.0211 mol), Meldrum acid (3.66 g, 0.0253 mol), 4-dimethylaminopyridine (3.92 g, 0.0316 mol) and anhydrous dichloromethane (100 mL). After the reaction mixture was cooled to 0 °C, EDCI-HCl (6.01 g, 0.0316 mol) was added to the same flask. The reaction mixture was stirred at room temperature for 12 hours. After completion of the reaction, the reaction mixture was diluted with dichloromethane and washed with 5% aqueous potassium bisulfate. The organic layer was separated, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give the crude product. The crude product was dissolved in ethyl acetate (100 mL) and refluxed for 4 hours. The volatiles were evaporated under reduced pressure to give tert-butyl 2,4-dioxopiperidine-1-carboxylate (3.2 g, 71% yield). 1H NMR (300 MHz, CDCl3): δ 4.12 (t, 2H), 3.51 (s, 2H), 2.64 (t, 2H), 1.55 (s, 9H). LCMS: 211.9 (M-H)+.

References

[1] Patent: WO2015/101928, 2015, A1. Location in patent: Page/Page column 52; 53
[2] Angewandte Chemie - International Edition, 2014, vol. 53, # 14, p. 3594 - 3598
[3] Angew. Chem., 2014, vol. 126, # 14, p. 3668 - 3672,5
[4] European Journal of Organic Chemistry, 2014, vol. 2014, # 34, p. 7651 - 7657

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