- Oxidative α-Trichloromethylation of Tertiary Amines: An Entry to α-Amino Acid Esters
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α-Trichloromethylation of tertiary amines with trimethyl(trichloromethyl)silane by oxidative coupling, using DDQ as an oxidant, has been realized. The reaction is instantaneous, is scalable, and tolerates a broad range of functional groups and heteroarenes. The trichloromethylated products can be easily converted into β,β-dichloroamines, enamines, and α-amino acid esters under operationally simple conditions. This methodology provides an efficient alternative to the poisonous cyanation reactions for the synthesis of carboxylic acid and their derivatives.
- Xu, Changming,Zhu, Zhaobin,Wang, Yongchang,Jing, Zhiguo,Gao, Bin,Zhao, Li,Dong, Wen-Kui
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- A process for the preparation of the new process prasugrel hydrochloride
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The invention discloses a novel synthesis process of prasugrel. The novel synthesis process comprises the steps: firstly, carrying out benzyl protection by taking 4, 5, 6, 7-tetrahydrothieno[3, 2-c]pyridine, benzaldehyde and sodium triacetoxyborohydride as starting raw materials to generate 5-benzyl-4, 5, 6, 7-tetrahydrothieno[3, 2-c]pyridine; then, brominating the 5-benzyl-4, 5, 6, 7-tetrahydrothieno[3, 2-c]pyridine by using hydrobromic acid to obtain 2-bromo-5-benzyl-4, 5, 6, 7-tetrahydrothieno[3, 2-c]pyridine; next, catalytically synthesizing 2-acetoxy-5-benzyl-4, 5, 6, 7-tetrahydrothieno[3, 2-c]pyridine by taking palladium acetate as a catalyst and XPhos as a ligand; and finally, carrying out hydrodebenzylation, and coupling the product with alpha-bromo-o-fluorobenzyl cyclopropyl ketone to obtain a target molecule 2-acetoxy-5-(alpha-cyclopropylcarbonyl-2-fluorobenzyl)-4, 5, 6, 7-tetrahydrothieno[3, 2-c]pyridine hydrochloride, i.e., the prasugrel hydrochloride. The process is simple, convenient and novel in route, easy to obtain raw materials, mild in condition, convenient to operate, high in total yield up to 80-90% and suitable for large-scale production.
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Paragraph 009; 0019; 0020
(2018/09/02)
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- Efficient synthesis of prasugrel, a novel P2Y12 receptor inhibitor
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An efficient synthesis of prasugrel, a novel P2Y12 receptor inhibitor, is described. The cyclopropyl-phenylethanone intermediate was prepared by cyanide substitution, bromination, N-substitution, and the Grignard reaction. After acid hydrolyzation of the methyl ether and subsequent acetylation, the title product was obtained with a total yield of 21% after 10 linear steps from simple and commercially available raw materials.
- Pan, Xianhua,Huang, Rui,Zhang, Jianshui,Ding, Liping,Li, Weijin,Zhang, Qunhui,Liu, Feng
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p. 5364 - 5366
(2012/10/29)
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- USE OF MERCAPTOACETALDEHYDE DIMER IN A NOVEL THIENOANNELATION SEQUENCE. A SHORT SYNTHESIS OF TICLOPIDINE
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A short synthesis of ticlopidine (1) was achieved by condensation of mercaptoacetaldehyde dimer (2) with piperidone (3b) in the presence of lithium diisopropylamide followed by dehydration.
- Gooding, Owen W.,Beard, Colin C.
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p. 1777 - 1780
(2007/10/02)
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- Synthesis of thienopyridine and furopyridine derivatives of therapeutic interest
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5-Benzyl-4,5,6,7-tetrahydrothieno [3,2-c] pyridines and analogous furopyridines were synthesized by NaBH4 reduction of the corresponding quaternary ammonium salts (method A). In the former series, the same derivatives were obtained by condensing benzyl halides with tetrahydrothienopyridine (method B).
- Maffrand,Eloy
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p. 483 - 486
(2007/10/05)
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