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Aminocyclanols, II: Stereochemical Studies on a New Ciramadol Analogue by NMR‐Spectroscopy
Author(s) -
Burgemeister Thomas,
Wiegrebe Wolfgang,
Ertan Mevlüt,
Akgün Hülya,
Özarslan Özdemir
Publication year - 1994
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.19943271206
Subject(s) - chemistry , isopropyl , stereochemistry , menthone , nuclear magnetic resonance spectroscopy , pyrrolidine , stereoselectivity , organic chemistry , menthol , catalysis
The absol. configuration of a Ciramadol analogue obtained from (‐)‐menthone is established by 1 H‐NMR‐, simulated NMR‐, COSY‐90‐, and NOE‐measurements. The final compound 2‐(α‐1‐pyrrolidino)benzyl‐4‐isopropyl‐1‐methyl‐cyclohexan‐3‐one ( 4b ), e.g. , has 1 R ,2 S ,4 S ,11 S ‐configuration due to stereoselective Michael ‐type addition of pyrrolidine to the pertinent benzylidene intermediate 3 .