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Synthesis of (S)‐3,4‐Diaminobutanenitriles as Precursors for 3‐Amino‐GABA Derivatives
Author(s) -
Gmeiner Peter,
Hummel Evi,
Haubmann Christian,
Höfner Georg
Publication year - 1995
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19953280311
Subject(s) - mitsunobu reaction , chemistry , reductive amination , aldehyde , asparagine , natural product , amination , derivative (finance) , amino acid , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry , catalysis , financial economics , economics
Starting from natural asparagine ( 1 ) a synthesis of the protected (S)‐3,4‐diaminobutanenitriles 5 and 8a – c via the β‐homoserine derivative 2 is described. The amino function in position 4 was introduced by Mitsunobu ‐coupling or by reductive amination when a strange deformylation of the amino aldehyde 7 was observed as a side reaction. The Mitsunobu ‐product 5 was converted into the dibenzylamine substituted GABA 6b which was investigated for its affinity at the GABA‐A receptor.