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Stereospezifische Synthese und Isomerisierung der 10‐Chlor‐decahydroisochinoline. Decahydroisochinoline. IV. Teil
Author(s) -
Grob C. A.,
Wohl R. A.
Publication year - 1966
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19660490804
Subject(s) - chemistry , chloride , formaldehyde , medicinal chemistry , acetic acid , aqueous solution , hydrogen chloride , isomerization , ring (chemistry) , catalysis , stereochemistry , organic chemistry
Treatment of cis‐ and trans ‐10‐hydroxy‐N‐methyl‐decahydroisoquinoline, ( 3a ) and ( 10a ) respectively, or N‐methyl‐Δ 9,10 ‐octahydroisoquinoline ( 4 a ) with hydrogen chloride in acetic acid affords the thermodynamically more stable trans ‐isomer of 10‐chloro‐N‐methyl‐decahydroisoquinoline ( 1a ). On the other hand ring closure of β‐(cyclohexen‐1‐yl)‐ethylamines 11a or 11b with aqueous formaldehyde in the presence of chloride ions leads to the 10‐ cis ‐chlorides 2a or 2b in a kinetically controlled reactions.