Short and Simple Synthesis of (r)-4-hydroxypentylaminoacetamide and (s)-4-hydroxypentylaminoacetamide - Both Enantiomers of the (omega-1)-hydroxylated Metabolite of Milacemide

Gorissen, HJ.;Vanhoeck, JP.;Mockel, AM.;Journee, GH.;Libert, VR.;et.al.
(1992) Chirality : the pharmacological, biological, and chemical consequences of molecular asymmetry — Vol. 4, n° 5, p. 286-294 (1992)

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  • Gorissen, HJ.
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  • Vanhoeck, JP.
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  • Mockel, AM.
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  • Journee, GH.
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  • Libert, VR.
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Abstract
Both (R)- and (S)-4-hydroxypentylaminoacetamide have been synthesized by reductive amination of glycinamide on the gamma-valerolactols corresponding to (R)- and (S)-gamma-valerolactone, respectively. These enantiomeric lactones were readily obtained in high enantiomeric excess (ee) by enzymic porcine pancreatic lipase (PPL) kinetic resolution of rac-methyl gamma-hydroxyvalerate.
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Gorissen, HJ., Vanhoeck, JP., Mockel, AM., Journee, GH., Delatour, C., & Libert, VR. (1992). Short and Simple Synthesis of (r)-4-hydroxypentylaminoacetamide and (s)-4-hydroxypentylaminoacetamide - Both Enantiomers of the (omega-1)-hydroxylated Metabolite of Milacemide. Chirality : the pharmacological, biological, and chemical consequences of molecular asymmetry, 4(5), 286-294. https://doi.org/10.1002/chir.530040505 (Original work published 1992)