(R)-1-(1-((S)-TETRAHYDRO-2H-PYRAN-3-YL)-1,6-DIHYDROIMIDAZO[4,5-D]PYRROLO[2,3-B]PYRIDIN-2-YL)ETHANOL synthesis

Yield:-

Steps:

Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 20 h / 23 - 75 °C / Inert atmosphere
2.1: hydrogen; palladium on activated charcoal / ethyl acetate / 48 h / 23 °C
3.1: triethyloxonium tetrafluoroborate / tetrahydrofuran / 1 h / 23 °C / Inert atmosphere
3.2: 2 h / 67 °C / Inert atmosphere
4.1: sodium hydroxide; water / ethanol / 1 h / 60 °C / Inert atmosphere

References:

Zak, Mark;Hurley, Christopher A.;Ward, Stuart I.;Bergeron, Philippe;Barrett, Kathy;Balazs, Mercedesz;Blair, Wade S.;Bull, Richard;Chakravarty, Paroma;Chang, Christine;Crackett, Peter;Deshmukh, Gauri;Devoss, Jason;Dragovich, Peter S.;Eigenbrot, Charles;Ellwood, Charles;Gaines, Simon;Ghilardi, Nico;Gibbons, Paul;Gradl, Stefan;Gribling, Peter;Hamman, Chris;Harstad, Eric;Hewitt, Peter;Johnson, Adam;Johnson, Tony;Kenny, Jane R.;Koehler, Michael F. T.;Bir Kohli, Pawan;Labadie, Sharada;Lee, Wyne P.;Liao, Jiangpeng;Liimatta, Marya;Mendonca, Rohan;Narukulla, Raman;Pulk, Rebecca;Reeve, Austin;Savage, Scott;Shia, Steven;Steffek, Micah;Ubhayakar, Savita;Van Abbema, Anne;Aliagas, Ignacio;Avitabile-Woo, Barbara;Xiao, Yisong;Yang, Jing;Kulagowski, Janusz J. [Journal of Medicinal Chemistry,2013,vol. 56,# 11,p. 4764 - 4785]