Multigram‐scale enzymatic kinetic resolution of trans‐2‐azidocyclohexyl acetate and chiral reversed‐phase HPLC analysis of trans‐2‐azidocyclohexanol

Lipase‐catalyzed hydrolytic kinetic resolution is a method of obtaining optically pure chiral alcohols and amines, which requires additional tools for determining enantiomerical purity. Herein, we present a study on multigram‐scale hydrolytic kinetic resolution of trans‐2‐azidocyclohexyl acetate usi...

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Bibliographic Details
Published in:Chirality (New York, N.Y.) N.Y.), 2022-02, Vol.34 (2), p.428-437
Main Authors: Hebda, Paulina, Wiśniowska, Lilianna, Szafrański, Przemysław W., Cegła, Marek
Format: Article
Language:English
Subjects:
2‐azidocyclohexanol
Acetates
Acetic acid
Alcohols
Amines
Calcium ions
chiral RP‐HPLC
Chromatography, High Pressure Liquid - methods
Fmoc derivatization
Fmoc ester
High performance liquid chromatography
hydrolytic kinetic resolution
Lipase
Lipase - chemistry
Liquid chromatography
Stereoisomerism
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Summary:Lipase‐catalyzed hydrolytic kinetic resolution is a method of obtaining optically pure chiral alcohols and amines, which requires additional tools for determining enantiomerical purity. Herein, we present a study on multigram‐scale hydrolytic kinetic resolution of trans‐2‐azidocyclohexyl acetate using Pseudomonas cepacia lipase immobilized on Immobead support. We investigated several parameters of the preparative‐scale process: temperature, organic co‐solvent, and the influence of calcium ions. Moreover, we have developed an efficient fluorenylmethyloxycarbonyl chloride (Fmoc‐Cl) derivatization protocol for 2‐azidocyclohexanol, which enabled chiral reversed‐phase high‐performance liquid chromatography (RP‐HPLC) determination of enantiomeric excess.
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.23397