1996
DOI: 10.1080/00397919608003527
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Efficient Synthesis of (S)-4(5)-[1-(2,3-Dimethylphenyl) ethyl]imidazole tartrate, the Potent α2Adrenoceptor Agonist Dexmedetomidine

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Cited by 16 publications
(12 citation statements)
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“…Thus, on a »50 mmol scale, a total volume of 125 mL ethanol was used at 5 C for a total stirring time of 16 h to perform one diasteroisomeric step and three consecutive fractional crystallizations to obtain dexmedetomidine with an overall yield of 26% and an enantiomeric excess of 99% as described in the Experimental Section. In contrast to previous results, 9,26 our optimized 144 Fakhraian et al…”
Section: Synthesis and Enantiomeric Resolution Of Medetomidine 143contrasting
confidence: 75%
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“…Thus, on a »50 mmol scale, a total volume of 125 mL ethanol was used at 5 C for a total stirring time of 16 h to perform one diasteroisomeric step and three consecutive fractional crystallizations to obtain dexmedetomidine with an overall yield of 26% and an enantiomeric excess of 99% as described in the Experimental Section. In contrast to previous results, 9,26 our optimized 144 Fakhraian et al…”
Section: Synthesis and Enantiomeric Resolution Of Medetomidine 143contrasting
confidence: 75%
“…25-Dexmedetomidine was obtained by resolution of ( §)-medetomidine via fractional crystallization of its diastereoisomeric salt with (C)-tartaric acid (as resolving agent) in alcoholic media. 9,26 The various parameters (temperature, stirring time and solvent amount) for this process also determined by the Taguchi method, were used to optimize the diastetreoisomeric resolution of medetomidine. The results indicate that temperature, stirring time and volume of solvent play significant roles in the generation of enantiomeric excesses.…”
Section: Synthesis and Enantiomeric Resolution Of Medetomidine 143mentioning
confidence: 99%
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“…(Cordi et al, 1996) (Scheme 3) The addition at the protected imidazolecarbaldehyde (13) proceeds however only in rather unsatisfactory yield of 52 %. In the next step a relatively cheap oxidant (pyrolusite) is used to convert the prepared secondary alcohol to the ketone (14), needed in the subsequent addition of methylmagnesium bromide.…”
Section: Introductionmentioning
confidence: 99%
“…The administration of local anaesthetics in the form of a free base or in the ionized state can induce analgesia either by general physicochemical disturbance of the neuron myelin sheath or by closing ionic sodium channels in the neuronal membrane [5]. The synthesis and characterization of medetomidine and dexmedetomidine have been well established [6][7][8][9][10]. The structural and thermal properties of the racemate drug and its hydrated form are well studied [11].…”
Section: Introductionmentioning
confidence: 99%