Short and simple synthesis of (R)- and (S)-4-hydroxypentylaminoacetamide: both enantiomers of the (ω-1)-hydroxylated metabolite of milacemide

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 pancre...

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Veröffentlicht in:	Chirality (New York, N.Y.) N.Y.), 1992, Vol.4 (5), p.286-294
Hauptverfasser:	Gorissen, Hugo J., Van Hoeck, Jean-Pierre, Mockel, Anne M., Journée, Guido H., Delatour, Claude, Libert, Valéry R.
Format:	Artikel
Sprache:	eng
Schlagworte:	(-)-(1S)-camphanyl diastereomeric derivatives 1H-NMR shift reagent Anticonvulsants. Antiepileptics. Antiparkinson agents Biological and medical sciences cytochrome P-450 enantiomers enzymic kinetic resolution hydroxylation Medical sciences metabolites milacemide Neuropharmacology Pharmacology. Drug treatments solid solution γ-valerolactone
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container_title	Chirality (New York, N.Y.)
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creator	Gorissen, Hugo J. Van Hoeck, Jean-Pierre Mockel, Anne M. Journée, Guido H. Delatour, Claude Libert, Valéry R.
description	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.
doi_str_mv	10.1002/chir.530040505
format	Article
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Antiparkinson agents</topic><topic>Biological and medical sciences</topic><topic>cytochrome P-450</topic><topic>enantiomers</topic><topic>enzymic kinetic resolution</topic><topic>hydroxylation</topic><topic>Medical sciences</topic><topic>metabolites</topic><topic>milacemide</topic><topic>Neuropharmacology</topic><topic>Pharmacology. Drug treatments</topic><topic>solid solution</topic><topic>γ-valerolactone</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gorissen, Hugo J.</creatorcontrib><creatorcontrib>Van Hoeck, Jean-Pierre</creatorcontrib><creatorcontrib>Mockel, Anne M.</creatorcontrib><creatorcontrib>Journée, Guido H.</creatorcontrib><creatorcontrib>Delatour, Claude</creatorcontrib><creatorcontrib>Libert, Valéry R.</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Chirality (New York, N.Y.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gorissen, Hugo J.</au><au>Van Hoeck, Jean-Pierre</au><au>Mockel, Anne M.</au><au>Journée, Guido H.</au><au>Delatour, Claude</au><au>Libert, Valéry R.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Short and simple synthesis of (R)- and (S)-4-hydroxypentylaminoacetamide: both enantiomers of the (ω-1)-hydroxylated metabolite of milacemide</atitle><jtitle>Chirality (New York, N.Y.)</jtitle><addtitle>Chirality</addtitle><date>1992</date><risdate>1992</risdate><volume>4</volume><issue>5</issue><spage>286</spage><epage>294</epage><pages>286-294</pages><issn>0899-0042</issn><eissn>1520-636X</eissn><coden>CHRLEP</coden><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.</abstract><cop>New York</cop><pub>Alan R. Liss, Inc</pub><doi>10.1002/chir.530040505</doi><tpages>9</tpages></addata></record>
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subjects	(-)-(1S)-camphanyl diastereomeric derivatives 1H-NMR shift reagent Anticonvulsants. Antiepileptics. Antiparkinson agents Biological and medical sciences cytochrome P-450 enantiomers enzymic kinetic resolution hydroxylation Medical sciences metabolites milacemide Neuropharmacology Pharmacology. Drug treatments solid solution γ-valerolactone
title	Short and simple synthesis of (R)- and (S)-4-hydroxypentylaminoacetamide: both enantiomers of the (ω-1)-hydroxylated metabolite of milacemide
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