138043-00-2Relevant academic research and scientific papers
Synthesis and structural and conformational study of some esters derived from 8-β-hydroxy-3-phenethyl-3-azabicyclooctan-8-α-carboxylic acid
Diez, M.,Izquierdo, M. L.,Arias, M. S.,Galvez, E.,Matesanz, E.,Martinez-Ripoll, M.
, p. 203 - 220 (1991)
A series of 8-β-hydroxy-8-α-alkoxycarbonyl-N-phenethyl-3-azabicyclooctane derivatives have been synthesized and studied by IR, 1H and 13C NMR spectroscopy, and the crystal structure of ethyl-8-β-hydroxy-3-phenethyl-3-azabicyclooctan-8-α-carboxylate (Va) has been determined by X-ray diffraction.In deuterochloroform and deuterobenzene the cyclopentane and piperidine rings of the title compounds show an envelope conformation flattened at C8 and a distorted chair conformation puckered at C8 and flattened at N3, respectively, with the N-substituent in an equatorial position.These results are in close agreement with that found for compound Va in the crystalline state.By comparing the NMR and X-ray parameters of the title compounds with those of the corresponding 8-α-hydroxy-8-β-alkoxycarbonyl-N-phenethyl-3-azabicyclooctane epimers and 3-phenethyl-3-azabicyclooctan-8-α- (and β)ol, several stereoelectronic effects have been deduced.
