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Synthesis of Substituted ( R p )‐2‐Aminomethyl‐1‐[( S )‐4‐isopropyloxazolin‐2‐yl]ferrocenes
Author(s) -
Šebesta Radovan,
Toma Štefan,
Sališová Marta
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200202)2002:4<692::aid-ejoc692>3.0.co;2-2
Subject(s) - chemistry , amine gas treating , nucleophile , iodide , methanol , group (periodic table) , leaving group , nucleophilic substitution , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis
The synthesis of novel N ‐substituted ( R p )‐2‐aminomethyl‐1‐[( S )‐4‐isopropyloxazolin‐2‐yl]ferrocenes is described. The usual synthesis by nucleophilic displacement of an acetoxy group with amine in methanol does not work in the case of the corresponding oxazolinylferrocene. This problem was solved by changing the leaving group to a pivaloyloxy group. Addition of water to the reaction media increases the yields and shortens the reaction times. We have also developed a new methodology for the direct conversion of the hydroxy group to an amine via an intermediate iodide.