831171-99-4Relevant articles and documents
Enantiomers of adrenaline-type amino alcohols by Burkholderia cepacia lipase-catalyzed asymmetric acylation
Lundell, Katri,Katainen, Erja,Kiviniemi, Anu,Kanerva, Liisa T.
, p. 3723 - 3729 (2007/10/03)
The enantiomers of norphenylephrine and octopamine were prepared using lipase PS-catalyzed enantioselective acylation with butanoic anhydride. Burkholderia cepacia lipase-catalyzed acylation with butanoic anhydride was used for the preparation of pharmaceutically important norphenylephrine and octopamine enantiomers, all in 98% ee. Reactivity of the phenolic OH groups and easy racemization, especially in the case of octopamine, complicated optimization. For norphenylephrine, chemical N-acylation was fast and allowed the subsequent enzymatic benzylic acylation in situ. The preparation of the octopamine enantiomers became possible by using the N-Fmoc protected substrate and by the Candida antarctica lipase B-catalyzed deprotection of the OH groups before the N-deprotection was performed.
