Title of article :
Facile and practical synthesis of a cannabinoid-1 antagonist via regio- and stereoselective ring-opening of an aziridinium ion
Author/Authors :
Edwin B. Villhauer، نويسنده , , Wen-Chung Shieh، نويسنده , , Zhengming Du، نويسنده , , Kevin Vargas، نويسنده , , Lech Ciszewski، نويسنده , , Yansong Lu، نويسنده , , Michael Girgis، نويسنده , , Melissa Lin، نويسنده , , Mahavir Prashad، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2009
Pages :
8
From page :
9067
To page :
9074
Abstract :
A scalable synthetic strategy of a chiral, trisubstituted imidazolidinone (1), a novel cannabinoid-1 antagonist, starting from a commercially available mandelic acid (5) is described. The key step involves a regio- and stereoselective ring-opening of an aziridinium ion by an aniline nucleophile (3). A mechanistic study revealed the insight into rate amplification at a lower temperature for vicinal diamine 12 formation via a aziridinium ion 14. Although most intermediates are not isolable by crystallization due to their intrinsic physical properties (oil or foamy solid), the reported synthesis furnished pure 1 without any chromatography purification throughout the entire synthesis. Employing green chemistry principles, this novel synthesis appears to be highly efficient for the manufacturing of multi-kilogram quantities of an optically-pure active pharmaceutical ingredient.
Keywords :
Regioselective , Stereoselective , aziridinium ion , imidazolidinone , Vicinal diamine
Journal title :
Tetrahedron
Serial Year :
2009
Journal title :
Tetrahedron
Record number :
1097878
Link To Document :
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