- Synthesis method of (R, S-) nicotine
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The invention belongs to the technical field of medical intermediates, and particularly relates to a synthesis method of (R, S-) nicotine. The method comprises the following steps: (1) taking methyl nicotinate and N-butenyl pyrrolidone as raw materials, and preparing N-butenyl-3-benzoyl-1-pyrrolidone through a condensation reaction; (2) after the reaction is finished, carrying out hydrolysis reaction, cooling, adjusting the pH value to be alkaline, extracting, separating out an organic phase, concentrating and distilling to obtain an enamine intermediate; and (3) carrying out a reduction reaction on the enamine intermediate under illumination with the wavelength of 200-400nm by using a metal oxide or a complex as a reduction catalyst to obtain the target product (R, S-) nicotine. According to the method, use of the metal catalyst is innovatively proposed, reaction is initiated by illumination with specific wavelength to prepare the (R, S-) nicotine, and the method is simple and convenient to operate, high in yield, low in cost and suitable for industrial large-scale production.
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- Highly chemoselective aerobic oxidation of amino alcohols into amino carbonyl compounds
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The direct oxidation of unprotected amino alcohols to their corresponding amino carbonyl compounds has often posed serious challenges in organic synthesis and has constrained chemists to adopting an indirect route, such as a protection/deprotection strategy, to attain their goal. Described herein is a highly chemoselective aerobic oxidation of unprotected amino alcohols to their amino carbonyl compounds in which 2-azaadamantane N-oxyl (AZADO)/copper catalysis is used. The catalytic system developed leads to the alcohol-selective oxidation of various unprotected amino alcohols, carrying a primary, secondary, or tertiary amino group, in good to high yield at ambient temperature with exposure to air, thus offering flexibility in the synthesis of nitrogen-containing compounds. Strong as an ox: The highly chemoselective aerobic oxidation of unprotected amino alcohols to their corresponding amino carbonyl compounds has been achieved by using 2-azaadamantane N-oxyl (AZADO)/copper catalysis. This catalytic system oxidizes not only alcohols with tertiary amino groups but also those with secondary and primary amines in good to high yield at ambient temperature in air. bpy=2,2-bipyridyl, DMAP=4-(N,N-dimethylamino)pyridine.
- Sasano, Yusuke,Nagasawa, Shota,Yamazaki, Mai,Shibuya, Masatoshi,Park, Jaiwook,Iwabuchi, Yoshiharu
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supporting information
p. 3236 - 3240
(2014/04/03)
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- PROCESS FOR THE PREPARATION OF (R,S)-NICOTINE
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A process for (R,S)-nicotine is described. Condensation of 1-(but-1-enyl)pyrrolidin-2-one with nicotinic acid ester gave 1-(but-1-enyl)-3-nicotinoylpyrrolidin-2-one which on treatment with an acid and a base gave myosmine. Myosmine was converted to (R,S)-nicotine by reduction followed by N-methylation.
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Page/Page column 2-3
(2012/08/28)
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