749247-37-8Relevant articles and documents
Functionalized 2,5-disubstituted benzazepines: Stereoselective synthesis of 3-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine-2-carbonitrile and related derivatives
Cobb, Jeff E.,Nanthakumar, Suganthini S.,Rutkowske, Randy,Uehling, David E.
, p. 1394 - 1398 (2007/10/03)
A stereoselective synthesis of 2-carbonitrile and 2-aminomethyl-substituted 5-phenylbenzazepine derivatives was developed starting from [4-hydroxy-3-(methyloxy)phenyl]acetic acid. The key step in the synthesis is a stereoselective addition of cyanide to 3-methyl-1-phenyl-2,3-dihydro-1H-3- benzazepine (4) to give a 15:1 trans/cis mixture of 2-carbonitrile-5-phenyl benzazepine diastereomers 5a/5b in 83% yield. The stereochemistry of the major product was deduced by 1H NMR NOESY analysis. The carbonitrile diastereomers could be separated and further manipulated by reduction to the corresponding aminomethyl derivatives 3a and 3b in a stereoselective manner. The aminomethyl benzazepine template 3 has potential to serve as a handle for the synthesis of a variety of derivatives modified at the 2-position of the benzazepine scaffold, as illustrated by an acylation of the primary amine of 3 followed by mild deprotection of the 7-phenol functionality.
