Description
N-Boc-3-Carboethoxy-4-piperidone has several applications in scientific research. It is used as a biochemical reagent, a pharmaceutical intermediate, and a building block in organic synthesis. In biochemical research, N-Boc-3-Carboethoxy-4-piperidone can be a substrate for various enzymes, such as proteases and glycosidases. It can also be used as a starting material for synthesising various pharmaceuticals, such as antibiotics and anti-inflammatory drugs. Finally, it can be used as a building block in organic synthesis, as it can be used to synthesize various polymers and other organic compounds.
Synthesis
Using ethyl 1-benzyl-4-oxo-3-piperidinecarboxylate hydrochloride (10.0 g, 33.6 mmol) and ethanol (800 mL) as the reaction system, a Pd/C catalyst (1.0 g, 10% w/w) was added and the hydrogenation reaction was carried out for about 15 h at room temperature. Upon completion of the reaction, triethylamine (19 mL, 134.3 mmol) and di-tert-butyl dicarbonate (8.0 g, 36.9 mmol) were added to the system, and stirring was continued at room temperature for 16 hours. The reaction mixture was filtered through diatomaceous earth to remove the catalyst and the filtrate was concentrated under vacuum and the residue was dissolved in dichloromethane and washed with water for extraction. The organic phase was separated, dried with anhydrous sodium sulfate and concentrated again in vacuum to give the final ethyl 1-N-Boc-4-oxo-3-piperidinecarboxylate (Compound IB, 9.11 g, 100% yield).
References
[1] Patent: WO2008/130584, 2008, A1. Location in patent: Page/Page column 131; 135
[2] Organic Process Research and Development, 2011, vol. 15, # 5, p. 1138 - 1148
[3] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 13, p. 3970 - 3975
[4] Patent: WO2011/103091, 2011, A1. Location in patent: Page/Page column 93
