专利号:US-11161827-B2 优先权日:2019-04-05 标 题 :Catalytic systems for stereoselective synthesis of chiral amines by enantiodivergent radical C—H amination 发明人:Zhang xiao-xiang; Lang kai 权利人:TRUSTEES BOSTON COLLEGE; THE TRUSTEES OF BOSTON COLLEGE 摘要:In one aspect, the disclosure relates to a mode of asymmetric induction in radical processes based on sequential combination of enantiodifferentiative H-atom abstraction and stereoretentive radical substitution. Also disclosed is an asymmetric system for stereoselective synthesis of strained 5-membered cyclic sulfamides via radical 1,5-C—H amination of sulfamoyl azides. The disclosed metalloradical system can control the degree and sense of asymmetric induction in the catalytic radical C—H amination in a systematic manner. The disclosed system is applicable to a broad scope of substrates with different types of C(sp 3 )—H bonds and exhibits reactivity and selectivity, providing access to both enantiomers of useful 5-membered cyclic sulfamides in a highly enantioenriched form. Also disclosed are catalysts useful in these processes. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present disclosure.
专利号:US-2004249170-A1 优先权日:2002-01-24 标 题 :Process for preparing an intermediate useful for the asymmetric synthesis of duloxetine 发明人:BORGHESE ALFIO 摘要:This invention provides a process for the synthesis of(S)-3-Methylamino-1-2-thienyl)-1-propanol, a key intermediate in the synthesis of duloxetine.
专利号:WO-2013008044-A1 优先权日:2011-07-08 标题:Synthesis of (+) and (-) 1 -(5,5-diphenyltetrahydrofuran-3- yl)-n,n-dimethylmethanamine, (+) and (-) 1-(2,2-diphenyltetrahydrofuran-3-yl)-n,n- dimethylmethanamine and (+) and (-) 1-(2,2- dffhenyltetrahydrofuran-3-yl)-n-metihylmethanamine 发明人:WAMVAKIDES ALEXANDRE; MOUTSOS VASSILIOS; SCHMITT MARTINE 权利人:ANAVEX LIFE SCIENCES CORP; WAMVAKIDES ALEXANDRE; MOUTSOS VASSILIOS; SCHMITT MARTINE 摘要:The current invention covers the synthesis of (+) and (-) l-(5,5-diphenyItetrahydrofuran-3- yl)-N,N-dimethylmethanamine [(±)1] and [(-)1] respectively, including their pharmacologically acceptable acid addition salts. The new products can be synthesized starting from 5,5-diphenyltetrahydrofuran-2(3H)-one (4) after insertion of an aldehyde group in the α-position, reduction to the prochiral 3-(hydroxymethyl)-1, 1-diphenylbutane-1,4-diol (6), chemoenzymatic desymmetrization using the enzyme Amano Lipase PS30, tosylation, intramolecular nucleophilic attack, hydrolysis, reaction with trifluoromethanesulfonic anhydride and substitution by dimethylamine, thus producing (+) 1-(5,5-diphenyl- tetrahydrofuran-3-yl)-N,N-dimethylmethanamine [(+)1]. Protection of the product of the chemoenzymatic desymmetrization with tert-butyldimethylsilyl chloride, hydrolysis, tosylation, intramolecular nucleophilic attack, removal of tert-butyldimethylsilyl group, reaction with trifluoromethanesulfonic anhydride and substitution by dimethylamine produces (-) 1-(5,5-diphenyltetrahydrofuran-3-yl)-N,N-dimethylmethanamine [(-)1]. It also covers the synthesis of (+) and (-) 1-(2,2-diphenyltetrahydrofuran-3-yl)-N,N- dimethylmethanamine [(+)2] and [(-)2] respectively and (+) and (-) 1-(2,2-diphenyl- tetrahydrofuran-3-yl)-N-methylmethanamine \\(+)3] and [(-)3] respectively, including their pharmacologically acceptable acid addition salts. The new products can be synthesized either starting from the reduction of 5-oxo-2,2-diphenyltetrahydrofuran-3-carboxylic acid (13) with LiA1H 4 , followed by the cyclization of the obtained triol (14) under acidic conditions, reaction with 1S-(-) or1R-(+)camphanic chloride, recrystallization, hydrolysis, reaction with trifluoromethanesulfonic anhydride and substitution by dimethylamine or methylamine, or by the reaction of R-(-) or S-(+) Mandelic acid and acetic acid with racemic 1-(2,2-diphenyltetrahydrofuran-3-yl)-N,N-dimethylmethanamine (2), recrystallization, followed by reaction with an aqueous solution of NaOH. The compounds mentioned in the invention present neuroprotective, antiepileptic and antidepressant activity and can be used as therapeutic agents.
专利号:WO-2011113486-A1 优先权日:2010-03-17 标 题 :Process for the synthesis of hydroxyphenylglycine esters 发明人:PALLARES BAYO ANTONIO; LOPEZ SANCHEZ RAMON; SANTIANDREU LOPEZ RICARDO MANUEL 权利人:DERETIL S A; PALLARES BAYO ANTONIO; LOPEZ SANCHEZ RAMON; SANTIANDREU LOPEZ RICARDO MANUEL 摘要:The present invention refers to a process for the synthesis of a D-(-)-p-hydroxyphenylglycine (HPG) ester in crystal form, by crystallizing D-HPG ester from a solution containing dissolved D-HPG ester to obtain a suspension comprising D-HPG ester crystals, characterized in that the ee D of the D-HPG ester in the solution and the ee D of the D-HPG ester crystals is above 95%, preferably above 97%, more preferably above 98%, more preferably above 99%, more preferably above 99.5%.
专利号:US-6472534-B2 优先权日:1999-10-21 标 题:Methods for the preparation of intermediates in the synthesis of HIV-protease inhibitors 发明人:BORER BENNETT C; ZOOK SCOTT E; BUSSE JULIETTE K 权利人:AGOURON PHARMA 摘要:Methods for the preparation of chemical intermediates in the synthesis of HIV-protease inhibitors related to and including nelfinavir mesylate are disclosed. The method of this invention comprises converting tetrohydran derivatives into oxazolines to provide key reaction intermediates for the preparation of nelfinavir. Also disclosed is a method for the preparation of a chiral amino alcohol from an epoxy-tetrahydrofuran.
专利号:US-6861416-B2 优先权日:2001-08-03 标题 :Oxazinones and methods for their use and synthesis 发明人:WOLFE SAUL; SHUSTOV GENNADY 权利人:CHIROLOGIX PHARMACEUTICALS INC 摘要:The invention pertains, at least in part, to new intermediates and synthetic methods for the stereospecific synthesis of oxazinone compounds, which are useful, for example, as antibiotics. The invention also pertains to novel olefinic oxazinone compounds, methods for their synthesis, and methods of using these compounds for the synthesis of oxazinones. The invention also pertains to methods for using the compounds to treat bacterial associated states in subjects.
摘要:Faber, K.; Glueck, S. M., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 1, 427. 摘要:Faber, K.; Glueck, S. M., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 1, 423. 摘要:Martínková, L.; Veselá, A. B., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 1, 286. 摘要:Bertau, M.; Jeromin, G. E., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 1, 178. 摘要:Oroz-Guinea, I.; Fernández-Lucas, J.; Hormigo, D.; García-Junceda, E., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 3, 449.