1-tert-Butyl 3-methyl 4-oxopiperidine-1,3-dicarboxylate Chemical Properties

Melting point:

32-34 °C

Boiling point:

350.0±42.0 °C(Predicted)

Density 

1.175±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

pka

11.06±0.20(Predicted)

Appearance

White to yellow Solid

InChI

InChI=1S/C12H19NO5/c1-12(2,3)18-11(16)13-6-5-9(14)8(7-13)10(15)17-4/h8H,5-7H2,1-4H3

InChIKey

HBWUTYLVFYVXML-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCC(=O)C(C(OC)=O)C1

Safety Information

HS Code 

2933399990

1-tert-Butyl 3-methyl 4-oxopiperidine-1,3-dicarboxylate Usage And Synthesis

Application

1-tert-butyl 4-oxopiperidinium-1,3-dicarboxylic acid ester and 3-methyl ester can be used as organic synthesis intermediates and pharmaceutical intermediates in laboratory research and development processes and chemical and pharmaceutical synthesis processes.

Chemical Properties

White to Light yellow powder to crystal

Synthesis

60% sodium hydride (3.5 g, 88 mmol) was suspended in anhydrous toluene (50 mL) at room temperature and protected by nitrogen. Dimethyl carbonate (4.32 g, 48.0 mmol) was added slowly and dropwise to this suspension over a period of 0.5 hours. After the addition of a few drops of methanol, a solution of N-tert-butoxycarbonyl-4-piperidone (4.8 g, 24 mmol) dissolved in anhydrous toluene (20 mL) was added dropwise to the reaction mixture while maintaining the reaction system at 80 °C with stirring. The reaction mixture was continued to be stirred at the same temperature for 3 h. The reaction mixture was subsequently cooled to 0 °C (ice bath) and the pH was adjusted to 6-6.5 with acetic acid. the resulting cold mixture was diluted with water (10 mL) and the pH was adjusted to 8 with 5% sodium hydroxide solution. the toluene layer was separated and the aqueous layer was extracted with toluene (20 mL). The combined organic layers were dried with anhydrous sodium sulfate and concentrated under reduced pressure. The product was dried under vacuum to afford methyl methyl-1-tert-butoxycarbonyl-4-oxo-3-piperidinecarboxylate (5.0 g, 80% yield). The resulting compound did not require further purification and could be used directly in the subsequent reaction.

References

[1] European Journal of Medicinal Chemistry, 2009, vol. 44, # 10, p. 4063 - 4069
[2] Patent: WO2016/123571, 2016, A1. Location in patent: Paragraph 00265
[3] Journal of the American Chemical Society, 2016, vol. 138, # 40, p. 13271 - 13280
[4] Journal of the American Chemical Society, 2015, vol. 137, # 21, p. 6738 - 6741
[5] Patent: CN107163045, 2017, A. Location in patent: Paragraph 0037; 0038

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