17862-85-0Relevant articles and documents
Transaminase-Mediated Amine Borrowing via Shuttle Biocatalysis
O'Reilly, Elaine,O'Sullivan, Rachel,Ryan, James,Taday, Freya
supporting information, (2022/01/04)
Shuttle catalysis has emerged as a useful methodology for the reversible transfer of small functional groups, such as CO and HCN, and goes far beyond transfer hydrogenation chemistry. While a biocatalytic hydrogen-borrowing methodology is well established, the biocatalytic borrowing of alternative functional groups has not yet been realized. Herein, we present a new concept of amine borrowing via biocatalytic shuttle catalysis, which has no counterpart in chemo-shuttle catalysis and allows efficient intermolecular amine shuttling to generate reactive intermediates in situ. By coupling this dynamic exchange with an irreversible downstream step to displace the reaction equilibrium in the forward direction, high conversion to target products can be achieved. We showcase the potential of this amine-borrowing methodology using a biocatalytic equivalent of both the Knorr-pyrrole synthesis and Pictet-Spengler reaction.
A 3 - (2 - amino-propyl) phenol preparation method (by machine translation)
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Paragraph 0041; 0042; 0043; 0055; 0056; 0069; 0070, (2017/08/28)
The invention discloses a 3 - (2 - amino-propyl) phenol preparation method, in order to methoxy bromophenylacetic, epoxy propane, methyl sulfonic acid, ammonia methanol and hydrobromic acid as the raw materials, through the four-step reaction to obtain the target product 3 - (2 - amino-propyl) phenol. The invention has simple operation, environment friendly, comprehensive yield is 63% more, than the existing 35.6% yield, with a remarkable enhancement, greatly reduces the production cost of the existing drugs, is suitable for industrial scale production. (by machine translation)
CAL-B-catalyzed resolution of some pharmacologically interesting β-substituted isopropylamines
Gonzalez-Sabin, Javier,Gotor, Vicente,Rebolledo, Francisca
, p. 1315 - 1320 (2007/10/03)
Some pharmacologically active amines such as amphetamine, the isomeric o-, m- and p-methoxyamphetamines, 4-phenylbutan-2-amine and mexiletine, as well as their corresponding acetamides, have been prepared in high yields and with very high enantiomeric excesses. The method consists of the Candida antarctica lipase B (CAL-B)-mediated enantioselective acetylation of racemic amines using ethyl acetate as solvent and acyl donor. The enzyme follows Kazlauskas' rule with all amines, (R)-amides being obtained as the major enantiomer in all cases. From the conversion values measured for both enantiomers, it can be deduced that the size of the substituents attached to the stereocenter is responsible for the enantioselectivity and rate of some of these reactions.