Process Development of Enantioselective Imine Reductase- Catalyzed Syntheses of Pharmaceutically Relevant Pyrrolidines

Bernhard LM, McLachlan J, Gröger H (2022)
Organic Process Research & Development 26(7): 2067–2074.

Zeitschriftenaufsatz | E-Veröff. vor dem Druck | Englisch
 
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Abstract / Bemerkung
Process development and optimization for an enzymatic reduction of 2-aryl-substituted pyrrolines to enantioselectively access the corresponding pyrrolidines have been carried out. Such chiral pyrrolidines are of high pharmaceutical interest and represent structural subunits in, e.g., larotrectinib and MSC2530818. This work enables access to the heterocyclic amine products with full conversion (>99%), excellent enantioselectivity (>99% ee), and good to high yield (up to 91%) in the presence of a readily available recombinant Escherichia coli-type whole-cell catalyst containing an imine reductase from Cupriavidus sp. HPC(L) and a glucose dehydrogenase in recombinant form. The developed processes utilizes cheap D-glucose as an economically favorable and nontoxic reducing agent and runs at a substrate loading of 18 g/L, which is also in an attractive range for larger-scale operations.
Stichworte
biocatalysis; CDK 8 inhibitor; enzymatic processes; imine reductases; larotrectinib
Erscheinungsjahr
2022
Zeitschriftentitel
Organic Process Research & Development
Band
26
Ausgabe
7
Seite(n)
2067–2074
ISSN
1083-6160
eISSN
1520-586X
Page URI
https://pub.uni-bielefeld.de/record/2964643

Zitieren

Bernhard LM, McLachlan J, Gröger H. Process Development of Enantioselective Imine Reductase- Catalyzed Syntheses of Pharmaceutically Relevant Pyrrolidines. Organic Process Research & Development. 2022;26(7):2067–2074.
Bernhard, L. M., McLachlan, J., & Gröger, H. (2022). Process Development of Enantioselective Imine Reductase- Catalyzed Syntheses of Pharmaceutically Relevant Pyrrolidines. Organic Process Research & Development, 26(7), 2067–2074. https://doi.org/10.1021/acs.oprd.1c00471
Bernhard, L. M., McLachlan, J., and Gröger, H. (2022). Process Development of Enantioselective Imine Reductase- Catalyzed Syntheses of Pharmaceutically Relevant Pyrrolidines. Organic Process Research & Development 26, 2067–2074.
Bernhard, L.M., McLachlan, J., & Gröger, H., 2022. Process Development of Enantioselective Imine Reductase- Catalyzed Syntheses of Pharmaceutically Relevant Pyrrolidines. Organic Process Research & Development, 26(7), p 2067–2074.
L.M. Bernhard, J. McLachlan, and H. Gröger, “Process Development of Enantioselective Imine Reductase- Catalyzed Syntheses of Pharmaceutically Relevant Pyrrolidines”, Organic Process Research & Development, vol. 26, 2022, pp. 2067–2074.
Bernhard, L.M., McLachlan, J., Gröger, H.: Process Development of Enantioselective Imine Reductase- Catalyzed Syntheses of Pharmaceutically Relevant Pyrrolidines. Organic Process Research & Development. 26, 2067–2074 (2022).
Bernhard, Laura Marie, McLachlan, Jill, and Gröger, Harald. “Process Development of Enantioselective Imine Reductase- Catalyzed Syntheses of Pharmaceutically Relevant Pyrrolidines”. Organic Process Research & Development 26.7 (2022): 2067–2074.

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