BioChem - DOS

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

Organic process research & development

Garcí a-Cerrada, Susana; Redondo-Gallego, Laura; Martí nez-Olid, Francisco; Rincó n, Juan A.; Garcí a-Losada, Pablo

<P>The diastereoselective preparation of <I>cis</I>- or <I>trans</I>-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 <I>cis</I>-allyl <I>N</I>-(4-hydroxy-1-methyl-cyclohexyl)carbamate (<B>6a</B>) via ketoreductase transformation. The methodology was also applicable to a set of different analogous cyclic ketones.</P><P><B>Graphic Abstract</B><BR><IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/oprdfk/2017/oprdfk.2017.21.issue-5/acs.oprd.7b00048/production/images/medium/op-2017-00048h_0008.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/op7b00048'>ACS Electronic Supporting Info</A></P>

2017

American Chemical Society

1083-6160

1520-586x

21

5

pp.779-784

10.1021/acs.oprd.7b00048

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