Synthesis
General procedure for the synthesis of ethyl 3-piperidine-4-propanoate from ethyl (E)-3-(pyridin-4-yl)acrylate: a mixture of ethyl (E)-3-(pyridin-4-yl)acrylate (3 g, 16.95 mmol) and a palladium/carbon catalyst (0.5 g) in methanol (30 mL) was stirred at 40°C under a hydrogen atmosphere of 276 kPa (40 Psi) The reaction was carried out overnight. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated in vacuum to afford ethyl 3-piperidine-4-propionate (3 g, 95.8% yield). The product was analyzed by electrospray ionization mass spectrometry (ESI-MS), and the molecular ion peak (M+H)+ was measured to be 186, which was in accordance with the theoretically calculated molecular weight of 185.2 for C10H19NO2.
References
[1] Patent: WO2014/131855, 2014, A1. Location in patent: Page/Page column 68
[2] Journal of the Chemical Society, 1951, p. 1406,1408
[3] Journal of the Chemical Society, 1951, p. 1406,1408
[4] Chemical and Pharmaceutical Bulletin, 1993, vol. 41, # 3, p. 529 - 538
[5] Chemical and Pharmaceutical Bulletin, 1986, vol. 34, # 9, p. 3747 - 3761
