Thermodynamic properties of the enantiomers of the Trˆger×s base as crystals and in ethanol solutions have been studied by means of a suite of analytical techniques. We report the melting diagrams of the two enantiomers, providing evidence for the formation of a solid racemic compound. We present also ternary equilibrium data about the solubility of the two enantiomers in ethanol at 258, 358, and 508. The melting-diagram data are described well by the SchroederÀVan Laar and PrigogineÀVieland equations, when the melting temperatures and enthalpies of pure enantiomer and of the racemic compound are provided and with the assumption that the melting behavior is ideal. The ternary equilibrium data were well-described when nonideality of mixtures of ethanol and the enantiomers is accounted for in terms of the non-random two liquids (NRTL) model. Finally, we present the newly determined X-ray crystal structure of an orthorhombic form of the pure Trˆger×s base ()-enantiomer.

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A concise catalytic asymmetric synthesis of idasanutlin (1) was developed in which the key pyrrolidine core, containing four contiguous stereocenters, was constructed via a Ag/MeOBIPHEP promoted [3 + 2] cycloaddition reaction. Further development of the [3 + 2] cycloaddition reaction resulted in an improvement in diastereoselectivity and enantioselectivity by changing the catalyst system to Cu­(I)/BINAP. While producing equivalent high quality API, the copper­(I) catalyzed process not only increased the overall yield but also demonstrated benefit with respect to cycle times, waste streams, and processability. The optimized copper­(I) catalyzed process has been used to prepare more than 1500 kg of idasanutlin (1).

Polymer electrolyte and solid oxide are the two fuel cell types (PEFC, SOFC) under development in Switzerland. The very distinct operating temperatures of 80°C (PEFC) and 800–950°C (SOFC) impose fundamentally different requirements upon the nature of the fuel; normally purified H2 for the former (CO trace) and usually synthesis gas for the latter (H2, CO as main constituents). Apart from stored hydrogen, the most relevant fuels are primary hydrocarbons (natural gas, biogas, liquids,...), that then need processing (chemical conversion, cleaning) up to a level compatible with the fuel cell catalysts. These processes are briefly reviewed. Fuel compositions with an emphasis on impurities are given. Two application examples from Swiss R&D are presented: gasoline conversion to high purity H2 for PEFC and contaminated biogas processing for SOFC.