Practical Manufacture of 4‑Alkyl-4-aminocyclohexylalcohols Using Ketoreductases

The diastereoselective preparation of cis- or trans-4-substituted-4-aminocyclohexyl alcohols by conventional chemical processes reported in the literature requires long synthetic sequences and is not amenable to scale-up. In the past decade, ketoreductases (KREDs) have emerged as a powerful approach...

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Bibliographic Details
Published in:Organic process research & development 2017-05, Vol.21 (5), p.779-784
Main Authors: García-Cerrada, Susana, Redondo-Gallego, Laura, Martínez-Olid, Francisco, Rincón, Juan A, García-Losada, Pablo
Format: Article
Language:English
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Summary:The diastereoselective preparation of cis- or trans-4-substituted-4-aminocyclohexyl alcohols by conventional chemical processes reported in the literature requires long synthetic sequences and is not amenable to scale-up. In the past decade, ketoreductases (KREDs) have emerged as a powerful approach for the preparation of chiral secondary alcohols from prochiral ketones. This paper describes the diastereoselective preparation at the kilo scale of cis-allyl N-(4-hydroxy-1-methyl-cyclohexyl)­carbamate (6a) via ketoreductase transformation. The methodology was also applicable to a set of different analogous cyclic ketones.
ISSN:1083-6160
1520-586X
DOI:10.1021/acs.oprd.7b00048