124573-98-4Relevant academic research and scientific papers
Safety assessment for the scale-up of an oxime reduction with melted sodium in standard pilot-plant equipment
Breitenmoser, Roland A.,Fink, Thomas,Abele, Stefan
, p. 2008 - 2014 (2012)
A pilot-plant process is described for the reduction of 2-allyl cyclohexanone oxime with melted sodium in xylenes, toluene, and 4-methyl-2-pentanol. The trans/cis ratio was 3-4:1. Safety data are presented from a range of thermokinetic experiments (heat flow calorimetry, differential scanning calorimetry, and accelerating rate calorimetry). The process has been designed and developed to enable an expedient and safe scale-up in a standard enameled 100-L steel reactor and has been reproduced six times on 209 mol scale (each 4.8 kg sodium). Crystallization of the product 2-allyl cyclohexylamine with oxalic acid from the reaction mixture in tert-butyl methyl ether successfully avoided the yield losses associated with the isolation of the volatile free 2-allyl cyclohexylamine.
The discovery of potent, selective, and orally bioavailable PDE9 inhibitors as potential hypoglycemic agents
DeNinno, Michael P.,Andrews, Melissa,Bell, Andrew S.,Chen, Yue,Eller-Zarbo, Cynthia,Eshelby, Nan,Etienne, John B.,Moore, Dianna E.,Palmer, Michael J.,Visser, Michael S.,Yu, Li J.,Zavadoski, William J.,Michael Gibbs
supporting information; experimental part, p. 2537 - 2541 (2009/12/25)
Starting from a non-selective pyrazolo-pyrimidone lead, the sequential use of parallel medicinal chemistry and directed synthesis led to the discovery of potent, highly selective, and orally bioavailable PDE9 inhibitors. The availability of these tools allowed for a thorough evaluation of the therapeutic potential of PDE9 inhibition.
SYNTHESIS OF MONOCYCLIC ANALOGUES OF A POTENT THROMBOXANE RECEPTOR ANTAGONIST, (+/-)-(5Z)-7-BICYCLOHEPT-2-EXO-YL>HEPTENOIC ACID (S-145)
Kawada, Kenji,Tsushima, Tadahiko
, p. 573 - 578 (2007/10/02)
Several monocyclic analogues of the potent thromboxane-A2 receptor antagonist S-145, i.e. cyclohexane, cyclopentane, tetrahydrofuran, and pyrrolidine, as well as the biclooctane one were synthesized using allylation via oxime dianion and the Barton's method for oxime reduction in the key steps.
