Large scale synthesis and absolute configuration of (-)-3-ppp, a selective dopamine autoreceptor agonist

Autor:	Seth-Olov Thorberg, Ingeborg Csöregh, Lars Gawell, J. L. G. Nilsson
Rok vydání:	1985
Předmět:	Aqueous solution Stereochemistry Chemistry Asymmetric carbon Yield (chemistry) Organic Chemistry Drug Discovery Absolute configuration Diastereomer Stereoselectivity Enantiomer Enantiomeric excess Biochemistry
Zdroj:	Tetrahedron. 41:129-139
ISSN:	0040-4020
DOI:	10.1016/s0040-4020(01)83477-3
Popis:	A large scale synthesis for (-)-3-PPP has been developed. The racemic methoxy compound 1 was prepared in a three step procedure in 63% yield. This was resolved as a diastereomeric salt by crystallization of the (-)-di-p-toluoyltartrate. Two crystallizations gave the pure (-)-enantiomer 2 in 50% of the theoretical yield and with an enantiomeric excess of >95%. Demethylation using aqueous HBr gave (-)-3-PPP, ( 3 ). Compound 2 was also prepared in a stereoselective synthesis from S -(-)- N-propyl-2- chloromethylpyrrolidine 4 . By X-ray crystallography it was shown that (-)-3-PPP has the S -configuration at the chiral carbon.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::10bcb8016c50c02d4516719416321464 https://doi.org/10.1016/s0040-4020(01)83477-3 Zobrazit plný text záznamu