CAS: 611-71-2; (R)-2-Hydroxy-2-Phenylacetic Acid

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在 Potassium Phosphate,Tris(2,2-Bipyridine)Ruthenium(II) Hexafluorophosphate,维生素 C体系中,用 水,乙腈 作为反应溶剂,化学反应 1.0H,以89%的收率获得产物d-扁桃酸
参考文献:Desyl和phenacyl作为多功能,光催化可裂解的保护基团:在不同(可见)光下的经典方法
标题:Desyl和phenacyl作为多功能,光催化可裂解的保护基团:在不同(可见)光下的经典方法
摘要:已经开发了使用可见光光氧化还原催化来脱保护经典苯甲酰基(pac)和去甲酰基(dsy)保护基的高效催化策略.故意使用具有k 3 Po 4的中性两相乙腈/水混合物,并施加催化量的[ru(bpy)3](pf 6)2与抗坏血酸结合使用是对pac和dsy保护的羧酸进行真正的催化脱保护的关键.我们温和而稳健的方案允许以非常好的定量产量快速而选择性地释放游离羧酸,而只需要低的催化剂负载量(1 Mol%).从市场上可买到的前体容易引入的pac和dsy均可用于直接保护羧酸和氨基酸,与许多其他常见的保护基团具有正交性.我们进一步证明了这些先前被低估的保护基团与我们的催化裂解条件相结合的普遍适用性和多功能性,这是由获得的高官能团耐受性所强调的.而且,该方法可以成功地适应固相合成的要求.作为有效可见光,光催化连接子裂解的原理证明,将boc保护的三肽从市售的溴化王树脂中分离出来.
DOI:10.1021/acscatal.7B02117

专利信息

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:WO-2023012205-A1
优先权日:2021-08-05
标 题 :Synthesis of specific butyrate compounds
发明人：BONRATH WERNER; GOETZINGER ALISSA; PACE FRANCESCO; WUESTENBERG BETTINA
权利人:DSM IP ASSETS BV
摘要:The present invention relates to new specific butyrate compounds to a new and improved synthesis of specific butyrates as well their use. Butyrate compounds are very useful compounds, either as such or as intermediates in organic synthesis.

专利号:WO-2010078250-A1
优先权日:2008-12-30
标 题:Synthesis of (2-amino)-tetrahydrocarbazole-propanoic acid
发明人：WEI YUAN; Li tianqiao; CHI YONGXIANG; ZHU JINGYANG
权利人:CHIRAL QUEST INC; WEI YUAN; Li tianqiao; CHI YONGXIANG; ZHU JINGYANG
摘要:The present invention provides a new approach to the synthesis of 2-amino-tetrahydrocarbazole-propanoic acid, a key intermediate for the synthesis of Ramatroban. More specifically, a synthesis of 2-amino-tetrahydrocarbazole- propanoic acid which includes oxidizing an aminocyclohexanol to form an aminocyclohexanone, condensing the aminocyclohexanone to form a tetrahydrocarbazole, deprotecting the tetrahydrocarbazole to yield a racemic mixture of a tetrahydrocarbazole, resolving the racemic mixture to obtain a yield mixture with an enantiomeric excess of one enantiomer over another, alkylating the excess enantiomer to yield an alkyl ester, and hydrolyzing the alkyl ester to yield 2-amino-tetrahydrocarbazole-propanoic acid.

专利号:WO-2019202611-A1
优先权日:2018-04-21
标题:An improved process for the synthesis of ivabradine and its pharmaceutically acceptable salts
发明人：NANDEPU Venkateswara Rao; BOPPANA DURGA PRASAD
权利人:METROCHEM API PVT
摘要:: Disclosed herein is an improved process for the preparation of Ivabradine and pharmaceutically acceptable salts thereof. The invention more particularly disclosesthe synthesis of key intermediates viz.,(S)-N-[(4,5-dimethoxybenzocydobut-l-yl)-methyl]-N- (methyl)amine hydrochloride of Formula-II and 3-(3-Iodopropyl)-7,8-dimethoxy-1,3-dihydro-2H-3-benzapin-2-one of Formula-III, and its use in industrial synthesis of Ivabradine and pharmaceutically acceptable salts thereof.

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:US-8791287-B2
优先权日:2010-07-02
标 题:Process for the synthesis of tapentadol and intermediates thereof
发明人：MOTTA GIUSEPPE; VERGANI DOMENICO; BERTOLINI GIORGIO; LANDONI NICOLA
权利人:MOTTA GIUSEPPE; VERGANI DOMENICO; BERTOLINI GIORGIO; LANDONI NICOLA; EUTICALS SPA
摘要:The object of the present invention is a new process for the synthesis of tapentadol, both as free base and in hydrochloride form, which comprises the step of alkylation of the ketone (VII) to yield the compound (VIII), as reported in Diagram 1, with high stereoselectivity due to the presence of the benzyl group as substituent of the amino group. It was surprisingly found that this substitution shifts the keto-enol equilibrium towards the desired enantiomer and amplifies the capacity of the stereocenter present in the compound (VII) to orient the nucleophilic addition of the organometallic compound at the carbonyl towards the desired stereoisomer. This substitution thus allows obtaining a considerable increase of the yields in this step, and consequently allows significantly increasing the overall yield of the entire tapentadol synthesis process. n A further object of the present invention is constituted by the tapentadol free base in solid form, obtainable by means of the process of the invention. n Still another object of the invention is represented by the crystalline forms I and II of the tapentadol free base. n A further object of the present invention is the mixture of the crystalline forms I and II of the tapentadol free base.