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

被引：1

作者：

Sherwood, Alexander M. ^{[1
]}

Burkhartzmeyer, Elise K. ^{[1
]}

Williamson, Samuel E. ^{[1
]}

Faley, Michael T. ^{[1
]}

机构：

[1] Usona Inst, Madison, WI 53711 USA

来源：

ACS OMEGA | 2023年 / 8卷 / 24期

关键词：

3,4-METHYLENEDIOXYMETHAMPHETAMINE; ECSTASY; 3,4-METHYLENEDIOXYAMPHETAMINE; DOPAMINE;

D O I：

10.1021/acsomega.3c02358

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A divergent two-step process has provided access to opticallypureenantiomers of MDMA and MDA, clinically relevant phenylisopropylamineentactogens. Target compounds were synthesized from commercially availablealanine-derived aziridines. Critical process parameters were identified,and the reactions were optimized to avoid chromatographic purificationstoward gram-scale isolations, providing (R)-(-)-MDMA,(S)-(+)-MDMA, (R)-(-)-MDA,and (S)-(+)-MDA each in greater than 98% purity byUPLC, >99% enantiomeric excess, and net yields between 50 and 60%for the complete process.

引用

页码：22132 / 22137

页数：6