40499-83-0Relevant articles and documents
Synthesis method of (R)-3-hydroxypyrrolidine
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Paragraph 0021-0026, (2021/04/17)
The invention relates to the technical field of organic synthesis, in particular to a synthesis method of (R)-3-hydroxy pyrrolidine, which comprises the following steps: reacting Lhydroxyproline in a reaction medium at 80-160 DEG C under the action of a decarboxylation catalyst, and carrying out reduced pressure distillation after the reaction is completed, thereby obtaining the (R)-3-hydroxy pyrrolidine, and the carboxylic acid decarboxylation catalyst is selected from methyl isobutyl or cyclohexanone. The (R)-3-hydroxy pyrrolidine synthesis method provided by the invention uses the cheap, safe and non-toxic decarboxylation catalyst and the reaction medium which is easier to recover, achieves higher yield than the prior art, and is suitable for industrial large-scale production.
Redox Condensations of o-Nitrobenzaldehydes with Amines under Mild Conditions: Total Synthesis of the Vasicinone Family
Afanasyev, Oleg I.,Podyacheva, Evgeniya,Rudenko, Alexander,Tsygankov, Alexey A.,Makarova, Maria,Chusov, Denis
, p. 9347 - 9360 (2020/08/14)
A total synthesis of the vasicinone family of natural products from bulk chemicals was developed. Reductive condensation of o-nitrobenzaldehydes with amines utilizing iron pentacarbonyl as a reducing agent followed by subsequent oxidation leads to a great variety of polycyclic nitrogen-containing heterocycles under mild conditions. Enantiomerically pure vasicinone, rutaecarpine, isaindigotone, and luotonin were synthesized from readily available starting materials like hydroxyproline, nitrobenzaldehyde, pyrrolidine, and piperidine in two to four operational steps without chromatography. The antifungal activity of all products was tested.
A fang chanfu law compound and its preparation method, pharmaceutical composition and use thereof
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Paragraph 0022; 0023; 0024; 0025; 0026, (2018/03/02)
The invention relates to a new compound for conversion of auricular fibrillation, as shown in the general formula i in the specification (n in the formula is equal to 0 to 4), or pharmaceutically acceptable salt thereof. The invention also provides a novel compound used as a preventive medicine or therapeutic drug for atrial fibrillation, a preparation method and a pharmaceutical composition containing the compound.
Preparation method of 1-BOC-3-hydroxymethyl pyrrolidine
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Paragraph 0021; 0024, (2017/05/10)
The invention discloses a preparation method of 1-Boc-3-hydroxymethyl pyrrolidine. The preparation method uses epichlorohydrin as a raw material, 3-hydroxymethyl pyrrolidine is obtained through reduction and cyclization reaction, then the 1-Boc-3-hydroxymethyl pyrrolidine is prepared through Boc protection reaction, then 1-BOC-3-methyl formate pyrrolidine is prepared through carboxylation reaction and esterification reaction, and finally the 1-BOC-3-methyl formate pyrrolidine and lithium aluminum hydride are catalyzed by a catalyst to prepare the 1-BOC-3-hydroxymethyl pyrrolidine. The preparation method is high in product synthesis rate, high in product purity and low in production cost, and the raw materials are cheap and easy to obtain.
NOVEL PROCESS FOR THE PREPARATION OF (3SM-[2-(2 J-DIHYDRO-5- BENZOFURANYL?ETHYL]-α.α -DIPHENYL-3-PYRROLIDINEACETAMIDE HYDROBROMIDE
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Page/Page column 11; 15-16, (2009/11/29)
The present invention is directed to a novel, industrially viable and cost effective process for manufacturing (3 S)- 1 -[2-(2,3-Dihydro-5-benzofuranyl)ethyl]-a,a-diphenyl-3-pyrrolidineacetamide hydrobromide also known as Darifenacin hydrobromide.
IMPROVED PROCESS FOR PRODUCING DARIFENACIN
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Page/Page column 7; 9, (2009/11/29)
The present invention discloses an improved process for producing darifenacin, the process comprising decarboxylating (2S,4R)-4-hydroxy-2-pyrrolidine carboxylic acid followed by in situ tosylation to give l-tosyl-3-(R)-(-)-hydroxypyrrolidine, tosylating the l-tosyl-3-(R)-(-)-hydroxypyrrolidine with methyl-p-toluenesuolphonate to give l-tosyl-3- (S)-(-)-tosyloxy pyrrolidine, reacting l-tosyl-3-(S)-(-)-tosyloxy pyrrolidine with diphenyl acetonitrile in presence of a base to give 3-(S)-(+)-(l-cyano-l,l-diphenylmethyl)-l- tosylpyrrolidine, de-protecting 3-(S)-(+)-(l-cyano-l,l-diphenylmethyl)-l- tosylpyrrolidine in the presence of phenol in acidic medium to give 3-(S)-(+)-(l-cyano- 1,1-diphenylmethyl) pyrrolidine, hydrolyzing 3-(S)-(+)-(l-cyano-l,l-diphenylmethyl) pyrrolidine followed by salt formation to obtain 3-(S)-(+)-(l-carbamoyl-l,l- diphenylmethyl)pyrrolidine.L-(+)-tartrate, condensing 3-(S)-(+)-( 1 -carbamoyl- 1,1- diphenylmethyl)pyrrolidine-L(+)-tartrate with 5-(2-bromoethyl)-2,3-dihydrobenzofuran employing a base in a solvent to give darifenacin.
PROCESS FOR PRODUCTION OF BENZYLOXYPYRROLIDINE DERIVATIVE, AND PROCESS FOR PRODUCTION OF HYDROCHLORIDE SALT POWDER OF OPTICALLY ACTIVE BENZYLOXYPYRROLIDINE DERIVATIVE
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Page/Page column 14, (2008/12/07)
Provided are: a process for production of a benzyloxypyrrolidine derivative in high yield and safety, and a process for production of a hydrochloride powder of a benzyloxypyrrolidine derivative in high yield and safety; the process for production of a benzyloxypyrrolidine derivative expressed by the general formula (2) [Chemical formula 2], in reacting a pyrrolidinol derivative represented by the general formula (1) [Chemical formula 1 with a benzyl halide derivative in the presence of an alkali metal hydroxide, wherein the reaction is carried out in either of the following conditions A or B; condition A: an aprotic polar solvent, and condition B: an aliphatic ether solvent containing a phase transfer catalyst:
PROCESS FOR THE PREPARATION OF CHIRAL 3-HYDROXY PYRROLIDINE COMPOUND AND DERIVATIVES THEREOF HAVING HIGH OPTICAL PURITY
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Page/Page column 21, (2010/11/26)
The present invention relates to an effective process for the preparation of optically pure chiral 3-hydroxypyrrolidine or derivatives thereof. More particularly, the present invention relates to an efficient process for the preparation of chiral 3-hydroxypyrrolidine or derivatives thereof, comprised of introducing a suitable protecting group to the starting material 4-chloro-3-hydroxybutyronitrile. Introduction of the hydroxy-protecting group provides advantages: efficient prevention of formation of side products, enhanced performance of the reduction of the nitrile group of the starting material, and enhanced performance of in-situ in? tramolecular cyclization. The chiral 3-hydroxypyrrolidine compound is produced in high yield and with high purity.
Synthesis of racemic and enantiomeric 3-pyrrolidinyl derivatives of nucleobases
Ko?alka, Petr,Pohl, Radek,Rejman, Dominik,Rosenberg, Ivan
, p. 5763 - 5774 (2007/10/03)
The synthesis of novel 3-pyrrolidinyl derivatives of nucleobases is described. Starting from malic acid, we improved the synthesis of both racemic and optically active N-benzyl-3-hydroxypyrrolidine-2,5-diones, which were transformed in four steps into N-tert-butyloxycarbonyl-3-mesyloxypyrrolidines, the key synthons for the alkylation of purine and pyrimidine nucleobases. Alkylations of cesium salts of purines and sodium salts of pyrimidines with N-tert-butyloxycarbonyl-3-mesyloxypyrrolidines proceeded smoothly, giving high yields of 9-substituted purine derivatives and moderate yields of 1-substituted pyrimidine derivatives. Using (S)-N-tert-butyloxycarbonyl-3-mesyloxypyrrolidine as the same intermediate for the synthesis of both enantiomeric N-Boc-3-pyrrolidinyladenines, and considering the results obtained on chiral HPLC analysis of the products, we proved that nucleophilic displacement of the mesyloxy group proceeded with inversion and not with retention of the configuration. Prepared compounds were tested for cytostatic and antiviral properties, but no significant activity was found.
Syntheses of ureas
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Page/Page column 18, (2010/02/15)
The present invention provides intermediates, synthetic methods and novel urea compositions of matter.
