510732-17-9Relevant articles and documents
Synthesis of N-acetyl-1,3-dimethyltetrahydroisoquinolines by intramolecular amidomercuration: Stereochemical aspects
De Koning,Michael, Joseph P.,Van Otterlo, Willem A. L.
, p. 2065 - 2067 (2002)
Mercury(II)-mediated ring closure of N-[1-(2-allyl-3-benzyloxy-4,6-dimethoxyphenyl)ethyl]acetamide 4 afforded N-acetyl-5-benzyloxy-6,8-dimethoxy- 1,3-trans-dimethyl-1,2,3,4-tetrahydroisoquinoline 3. The product was shown to exist as a mixture of rotamers by NMR spectroscopy, since signals coalesced at higher temperatures. 2-[2-[1-(Acetylamino)ethyl]-6-(benzyloxy)-3,5-dimethoxyphenyl]-1-methylethyl methanesulfonate 8 was also cyclized with sodium hydride to afford rotameric products with the same isoquinoline skeleton, but as a mixture of 1,3-cis- and transdimethyl isomers.