- 2-[(2R, 6S)-6-[(2S)-2-hydroxy-2-phenethyl]-1-pipecoline]-1-hypnone synthesis method
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The invention discloses a 2-[(2R, 6S)-6-[(2S)-2-hydroxy-2-phenethyl]-1-pipecoline]-1-hypnone synthesis method, and belongs to the field of organic synthesis. (1S, 2S)-1, 2-diphenyl diaminoethane serving as a raw material is subjected to acylation, substitution and the like to prepare chiral amine catalysts. A main route totally includes two steps: synthesizing glutaraldehyde, benzoyl acetic acid and methylamine hydrochloride to form cis-lobelanine; performing asymmetric selective reduction synthesis of 2-[(2R, 6S)-6-[(2S)-2-hydroxy-2-phenethyl]-1-pipecoline]-1-hypnone under mild reaction conditions and under the action of the catalysts. The raw material in the whole process route is cheap and easy to obtain, the catalysts can be recycled and can continue to be used, and the synthesis method is low in cost, simple in process, mild in reaction condition, convenient in operation and high in total yield.
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Paragraph 0043; 0044
(2017/06/02)
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- Thermodynamic epimeric equilibration and crystallisation-induced dynamic resolution of lobelanine, norlobelanine and related analogues
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The step-economical synthesis of lobelanine involving a ring closing double aza-Michael (RCDAM) reaction is revisited and successfully extended to the synthesis of various configurationally more stable analogues. Owing to the presence of a configurationally labile β-aminoketone subunit, lobelanine is prone to self-catalyze mutarotation in solution. Through the synthesis of original lobelanine analogues, we studied the influence of (i) the size of the central heterocycle, (ii) the bulkiness of the nitrogen protecting group, and (iii) the phenacyl arm substituent on the thermodynamic equilibrium and its displacement by crystallisation-induced dynamic resolution (CIDR). We demonstrated that fine structural tuning combined with optimized CIDR conditions favours the first efficient diastereoselective synthesis of lobelanine's analogues.
- Amara,Bernadat,Venot,Retailleau,Troufflard,Drge,Le Bideau,Joseph
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p. 9797 - 9810
(2015/01/08)
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