- Synthesis method of chiral 3-aminopiperidine and derivatives of 3-aminopiperidine
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The invention relates to a synthesis method of chiral 3-aminopiperidine and derivatives of 3-aminopiperidine. According to the synthesis method, R (or S)-piperidine-3-ethyl formate-L (or D)-tartrate is subjected to a hydrazinolysis reaction after being subjected to benzyl protection, and R or S-1-benzyl-3-aminopiperidine is obtained through azidation and Curtius rearrangement. R or S-1-benzyl-3-aminopiperidine is subjected to debenzylation, R or S-3-aminopiperidine can be obtained, R or S-1-benzyl-3-aminopiperidine is subjected to 3-t-butyloxycarboryl protection and debenzylation in sequence,R or S-(3-t-butyloxycarborylamino) piperidine can be obtained, and corresponding salts of R or S-3-aminopiperidine can be obtained through hydrolyzing deprotection of R or S-(3-t-butyloxycarborylamino) piperidine under the acidic condition. The synthesis method of chiral 3-aminopiperidine and the derivatives of 3-aminopiperidine is low in cost, facilitates industrialization and has high optical purity.
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Paragraph 0126-0127
(2019/09/17)
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- Asymmetric Hydrogenation of 3-Substituted Pyridinium Salts
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The use of an equivalent amount of an organic base leads to high enantiomeric excess in the asymmetric hydrogenation of N-benzylated 3-substituted pyridinium salts into the corresponding piperidines. Indeed, in the presence of Et3N, a Rh-JosiPhos catalyst reduced a range of pyridinium salts with ee values up to 90 %. The role of the base was elucidated with a mechanistic study involving the isolation of the various reaction intermediates and isotopic labeling experiments. Additionally, this study provided some evidence for an enantiodetermining step involving a dihydropyridine intermediate.
- Renom-Carrasco, Marc,Gajewski, Piotr,Pignataro, Luca,de Vries, Johannes G.,Piarulli, Umberto,Gennari, Cesare,Lefort, Laurent
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supporting information
p. 9528 - 9532
(2016/07/14)
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- Enantioselective addition of diethylzinc to aldehydes catalyzed by ethyl nipecotate- derived new chiral ligand
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(R)-(-)-Diphenyl-(N-methylpiperidin-3-yl)methanol (3) derived from (±)- ethyl nipecotate catalyzed the enantioselective addition of diethylzinc to various aldehydes in good to moderate optical yield (40% - 81%).
- Lee, So Ha,Im, Dai Sig,Cheong, Chan Seong,Chung, Bong Young
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p. 1913 - 1919
(2007/10/03)
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