Literature DB >> 28345159

Stereoselective Catalytic Synthesis of Active Pharmaceutical Ingredients in Homemade 3D-Printed Mesoreactors.

Sergio Rossi1, Riccardo Porta1, Davide Brenna1, Alessandra Puglisi1, Maurizio Benaglia1.   

Abstract

3D-printed flow reactors were designed, fabricated from different materials (PLA, HIPS, nylon), and used for a catalytic stereoselective Henry reaction. The use of readily prepared and tunable 3D-printed reactors enabled the rapid screening of devices with different sizes, shapes, and channel dimensions, aimed at the identification of the best-performing reactor setup. The optimized process afforded the products in high yields, moderate diastereoselectivity, and up to 90 % ee. The method was applied to the continuous-flow synthesis of biologically active chiral 1,2-amino alcohols (norephedrine, metaraminol, and methoxamine) through a two-step sequence combining the nitroaldol reaction with a hydrogenation. To highlight potential industrial applications of this method, a multistep continuous synthesis of norephedrine has been realized. The product was isolated without any intermediate purifications or solvent switches.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  3D printing; amino alcohols; flow reactors; nitroaldol reactions; stereoselective catalysis

Mesh:

Substances:

Year:  2017        PMID: 28345159     DOI: 10.1002/anie.201612192

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  7 in total

Review 1.  3D printing and continuous flow chemistry technology to advance pharmaceutical manufacturing in developing countries.

Authors:  Cloudius R Sagandira; Margaret Siyawamwaya; Paul Watts
Journal:  Arab J Chem       Date:  2020-09-23       Impact factor: 5.165

2.  Organocatalytic Michael Addition to (D)-Mannitol-Derived Enantiopure Nitroalkenes: A Valuable Strategy for the Synthesis of Densely Functionalized Chiral Molecules.

Authors:  Lucia Caruso; Alessandra Puglisi; Emmerance Gillon; Maurizio Benaglia
Journal:  Molecules       Date:  2019-12-14       Impact factor: 4.411

3.  Enantioselective Organophotocatalytic Telescoped Synthesis of a Chiral Privileged Active Pharmaceutical Ingredient.

Authors:  Fabian Herbrik; Miguel Sanz; Alessandra Puglisi; Sergio Rossi; Maurizio Benaglia
Journal:  Chemistry       Date:  2022-05-04       Impact factor: 5.020

4.  Manufacturing and Application of 3D Printed Photo Fenton Reactors for Wastewater Treatment.

Authors:  Kourosh Nasr Esfahani; Mohammad Damous Zandi; J Antonio Travieso-Rodriguez; Moisès Graells; Montserrat Pérez-Moya
Journal:  Int J Environ Res Public Health       Date:  2021-05-04       Impact factor: 3.390

5.  Revealing interactions of layered polymeric materials at solid-liquid interface for building solvent compatibility charts for 3D printing applications.

Authors:  Kirill S Erokhin; Evgeniy G Gordeev; Valentine P Ananikov
Journal:  Sci Rep       Date:  2019-12-27       Impact factor: 4.379

6.  Multigram-scale flow synthesis of the chiral key intermediate of (-)-paroxetine enabled by solvent-free heterogeneous organocatalysis.

Authors:  Sándor B Ötvös; Miquel A Pericàs; C Oliver Kappe
Journal:  Chem Sci       Date:  2019-10-18       Impact factor: 9.825

7.  Telescoped Continuous Flow Synthesis of Optically Active γ-Nitrobutyric Acids as Key Intermediates of Baclofen, Phenibut, and Fluorophenibut.

Authors:  Sándor B Ötvös; Patricia Llanes; Miquel A Pericàs; C Oliver Kappe
Journal:  Org Lett       Date:  2020-10-07       Impact factor: 6.005

  7 in total

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