Swim in the Chiral Pool: MDMA and MDA Enantiomers from Alanine-Derived Precursors

[Image: see text] A divergent two-step process has provided access to optically pure enantiomers of MDMA and MDA, clinically relevant phenylisopropylamine entactogens. Target compounds were synthesized from commercially available alanine-derived aziridines. Critical process parameters were identifie...

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Autores principales: Sherwood, Alexander M., Burkhartzmeyer, Elise K., Williamson, Samuel E., Faley, Michael T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10286248/
https://www.ncbi.nlm.nih.gov/pubmed/37360440
http://dx.doi.org/10.1021/acsomega.3c02358
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author Sherwood, Alexander M.
Burkhartzmeyer, Elise K.
Williamson, Samuel E.
Faley, Michael T.
author_facet Sherwood, Alexander M.
Burkhartzmeyer, Elise K.
Williamson, Samuel E.
Faley, Michael T.
author_sort Sherwood, Alexander M.
collection PubMed
description [Image: see text] A divergent two-step process has provided access to optically pure enantiomers of MDMA and MDA, clinically relevant phenylisopropylamine entactogens. Target compounds were synthesized from commercially available alanine-derived aziridines. Critical process parameters were identified, and the reactions were optimized to avoid chromatographic purifications toward gram-scale isolations, providing (R)-(−)-MDMA, (S)-(+)-MDMA, (R)-(−)-MDA, and (S)-(+)-MDA each in greater than 98% purity by UPLC, >99% enantiomeric excess, and net yields between 50 and 60% for the complete process.
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spelling pubmed-102862482023-06-23 Swim in the Chiral Pool: MDMA and MDA Enantiomers from Alanine-Derived Precursors Sherwood, Alexander M. Burkhartzmeyer, Elise K. Williamson, Samuel E. Faley, Michael T. ACS Omega [Image: see text] A divergent two-step process has provided access to optically pure enantiomers of MDMA and MDA, clinically relevant phenylisopropylamine entactogens. Target compounds were synthesized from commercially available alanine-derived aziridines. Critical process parameters were identified, and the reactions were optimized to avoid chromatographic purifications toward gram-scale isolations, providing (R)-(−)-MDMA, (S)-(+)-MDMA, (R)-(−)-MDA, and (S)-(+)-MDA each in greater than 98% purity by UPLC, >99% enantiomeric excess, and net yields between 50 and 60% for the complete process. American Chemical Society 2023-06-06 /pmc/articles/PMC10286248/ /pubmed/37360440 http://dx.doi.org/10.1021/acsomega.3c02358 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Sherwood, Alexander M.
Burkhartzmeyer, Elise K.
Williamson, Samuel E.
Faley, Michael T.
Swim in the Chiral Pool: MDMA and MDA Enantiomers from Alanine-Derived Precursors
title Swim in the Chiral Pool: MDMA and MDA Enantiomers from Alanine-Derived Precursors
title_full Swim in the Chiral Pool: MDMA and MDA Enantiomers from Alanine-Derived Precursors
title_fullStr Swim in the Chiral Pool: MDMA and MDA Enantiomers from Alanine-Derived Precursors
title_full_unstemmed Swim in the Chiral Pool: MDMA and MDA Enantiomers from Alanine-Derived Precursors
title_short Swim in the Chiral Pool: MDMA and MDA Enantiomers from Alanine-Derived Precursors
title_sort swim in the chiral pool: mdma and mda enantiomers from alanine-derived precursors
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10286248/
https://www.ncbi.nlm.nih.gov/pubmed/37360440
http://dx.doi.org/10.1021/acsomega.3c02358
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