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Nanopalladium-catalyzed conjugate reduction of Michael acceptors – application in flow

SYNTHESIS Comments Off

May 212016

Green Chem., 2016, 18,2632-2637
DOI: 10.1039/C5GC02920A, Communication

Anuja Nagendiran, Henrik Sorensen, Magnus J. Johansson, Cheuk-Wai Tai, Jan-E. Backvall
A continuous-flow approach towards the selective nanopalladium-catalyzed hydrogenation of the olefinic bond in various Michael acceptors, which could lead to a greener and more sustainable process, has been developed.

Nanopalladium-catalyzed conjugate reduction of Michael acceptors – application in flow

Communication

Nanopalladium-catalyzed conjugate reduction of Michael acceptors – application in flow

Anuja Nagendiran,^a^b Henrik Sörensen,^b^c Magnus J. Johansson,^b^c Cheuk-Wai Tai^d and Jan-E. Bäckvall*^a^b

*Corresponding authors

^aDepartment of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91 Stockholm, Sweden
E-mail: jeb@organ.su.se

Berzelii Centre EXSELENT on Porous Materials, Arrhenius Laboratory, Stockholm University, SE-106 91 Stockholm, Sweden

AstraZeneca R&D, Innovative Medicines, Cardiovascular and Metabolic Disorders, Medicinal Chemistry, Pepparedsleden 1, SE-431 83 Mölndal, Sweden

Department of Materials and Environmental Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91, Stockholm, Sweden

Green Chem., 2016,18, 2632-2637

DOI: 10.1039/C5GC02920A

http://pubs.rsc.org/en/Content/ArticleLanding/2016/GC/C5GC02920A?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

A continuous-flow approach towards the selective nanopalladium-catalyzed hydrogenation of the olefinic bond in various Michael acceptors, which could lead to a greener and more sustainable process, has been developed. The nanopalladium is supported on aminofunctionalized mesocellular foam. Both aromatic and aliphatic substrates, covering a variation of functional groups such as acids, aldehydes, esters, ketones, and nitriles were selectively hydrogenated in high to excellent yields using two different flow-devices (H-Cube® and Vapourtec). The catalyst was able to hydrogenate cinnamaldehyde continuously for 24 h (in total hydrogenating 19 g cinnanmaldehyde using 70 mg of catalyst in the H-cube®) without showing any significant decrease in activity or selectivity. Furthermore, the metal leaching of the catalyst was found to be very low (ppb amounts) in the two flow devices.

////////Nanopalladium-catalyzed, conjugate reduction, Michael acceptors, application, flow chemistry

Potential of Homogeneous Pd Catalyst Separation by Ceramic Membranes. Application to Downstream and Continuous Flow Processes

SYNTHESIS Comments Off

May 072016

Successful chemical production of molecules while simultaneously reducing the environmental impact of the process relies not only on more efficient reactions but also on developments in reactor and separation technology. Recent decades have also witnessed a significant growth in industrial interest in solvent-based separations using membranes stable to organic solvents. The incorporation of membranes into a chemical process can be via a simple downstream processing method or an integrated reaction membrane method. This paper deals with homogeneous organometallic catalyzed reactions and probes the separation of a number of readily available palladium complexes from reaction mixtures with highly stable ceramic membranes. A number of different processing methods, namely, online, at-line, and off-line are compared and contrasted. A high rejection of Palladium species and consequently very low palladium contamination of reaction products with a single organic solvent nanofiltration (OSN) step has been demonstrated.

Potential of Homogeneous Pd Catalyst Separation by Ceramic Membranes. Application to Downstream and Continuous Flow Processes

Dominic Ormerod^*^†, Nicolas Lefevre^‡, Matthieu Dorbec^†, Inge Eyskens^†, Pieter Vloemans^†, Karlien Duyssens^†, Veronica Diez de la Torre^†, Nadya Kaval^‡, Eugen Merkul^‡, Sergey Sergeyev^‡, and Bert U. W. Maes^‡

^† VITO (Flemish Institute for Technological Research), Separation and Conversion Technology, Boeretang 200, B-2400 Mol, Belgium

^‡ Organic Synthesis, University of Antwerp, Groenenborgerlaan 171, B-2020 Antwerp, Belgium

Org. Process Res. Dev., Article ASAP

DOI: 10.1021/acs.oprd.5b00418

http://pubs.acs.org/doi/abs/10.1021/acs.oprd.5b00418

//////Potential, Homogeneous Pd Catalyst Separation, Ceramic Membranes, Application, Downstream, Continuous Flow Processes

Application of On-Line NIR for Process Control during the Manufacture of Sitagliptin

PROCESS, spectroscopy, SYNTHESIS Comments Off

Mar 062016

The transamination-chemistry-based process for sitagliptin is a through-process, which challenges the crystallization of the active pharmaceutical ingredient (API) in a batch stream composed of multiple components. Risk-assessment-based design of experiment (DoE) studies of particle size distribution (PSD) and crystallization showed that the final API PSD strongly depends on the seeding-point temperature, which in turn relies on the solution composition.

To determine the solution composition, near-infrared (NIR) methods had been developed with partial least squares (PLS) regression on spectra of simulated process samples whose compositions were made by spiking each pure component, either sitagliptin free base (FB), water, isopropyl alcohol (IPA), dimethyl sulfoxide (DMSO), or isopropyl acetate (IPAc), into the process stream according to a DoE. An additional update to the PLS models was made by incorporating the matrix difference between simulated samples in lab and factory batches.

Overall, at temperatures of 20–35 °C, the NIR models provided a standard error of prediction (SEP) of less than 0.23 wt % for FB in 10.56–32.91 wt %, 0.22 wt % for DMSO in 3.77–19.18 wt %, 0.32 wt % for IPAc in 0.00–5.70 wt %, and 0.23 wt % for water in 11.20–28.58 wt %. After passing the performance qualification, these on-line NIR methods were successfully established and applied for the on-line analysis of production batches for compositions prior to the seeding point of sitagliptin crystallization.

see……..http://pubs.acs.org/doi/abs/10.1021/acs.oprd.5b00409