Short and simple synthesis of (R)- and (S)-4-hydroxypentylaminoacetamide: both enantiomers of the (ω-1)-hydroxylated metabolite of milacemide |
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| Authors: | Hugo J. Gorissen,Jean-Pierre Van Hoeck,Anne M. Mockel,Guido H. Journ e,Claude Delatour,Val ry R. Libert |
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| Affiliation: | Hugo J. Gorissen,Jean-Pierre Van Hoeck,Anne M. Mockel,Guido H. Journée,Claude Delatour,Valéry R. Libert |
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| Abstract: | Both (R)- and (S)-4-hydroxypentylaminoacetamide have been synthesized by reductive amination of glycinamide on the γ-valerolactols corresponding to (R)- and (S)-γ-valerolactone, respectively. These enantiomeric lactones were readily obtained in high enantiomeric excess (ee) by enzymic porcine pancreatic lipase (PPL) kinetic resolution of rac-methyl γ-hydroxyvalerate. © 1992 Wiley-Liss, Inc. |
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| Keywords: | milacemide metabolites enantiomers hydroxylation cytochrome P-450 γ -valerolactone enzymic kinetic resolution 1H-NMR shift reagent (– )-(1S)-camphanyl diastereomeric derivatives solid solution |
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