CAS: 5817-26-5; (S)-Ethyl Pyrrolidine-2-Carboxylate

该化合物是丙醇的手性酯衍生物,在有机合成和制药应用中广泛用作多用途中间体,其立体化学纯度对不对称合成,特别是生物活性化合物和手性辅助物的制作具有价值.乙基酯组增加了有机溶剂中的溶性,便利了其在诸如peptide 混合或核循环替代物等反应中的使用.该化合物常常用于合成活性模拟物,催化剂和离心剂,以进行不对称的催化.该化合物在标准条件下的稳定性和与不同反应条件的兼容性进一步强调了其在精密化学和药用化学研究中的实用性.

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相似化合物

33305-75-8 125347-83-3 131477-20-8

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ECHA物质C&L通报

上下游产品

ethanol L-prolineL-proline N-benzyl-L-proline ethyl ester L-proline ethyl ester monohydr°Chloride1-acetyl-prolin-ethyl ester (S)-diphenylprolinol imidazol-1-one3-thioxohexahydropyrrolo1,2-cimidazol-1-one (S)-1-Pyrrolidin-2-yl-methanol

合成工艺路线路线简述

    📜N-苄基-L-脯氨酸乙酯置于palladium 10% On Activated Carbon,氢气,1-Butyl-3-Methylimidazolium Tetrafluoroborate体系中,用 甲醇 作为反应溶剂,20.0 °C,101.33 Kpa 条件下,反应 12.0H,反应生成 (2S)-吡咯烷-2-羧酸乙酯
    参考文献:使用离子液体作为可回收 Pd/c 介导的 N-脱苄基化的助溶剂
    标题:使用离子液体作为可回收 Pd/c 介导的 N-脱苄基化的助溶剂
    摘要:1 Meoh Only 77 2 1A 34 3 1B 70 4 1C 82 5 1D 93 6 1E 96 在硅胶柱上纯化后的产量.剩余约 10% 的起始材料.苄基是肽和碳水化合物化学中广泛使用的氨基,羟基和硫氢基的保护基团.它作为保护基团的流行归因于它在各种反应条件下的化学稳定性,包括强酸性和碱性环境.然而,当涉及到其去保护时,苄基的这种强大特性有时会成为一种不利因素.对于 N-苄基的脱保护,已报道了多种方法,包括在高压或大气压下用 Pd/c 氢化,在酸性介质中或用甲酸铵催化转移氢化,用分子氧氧化,使用路易斯酸,或使用光敏单电子转移反应和使用其他试剂.除了使用甲酸铵的催化氢化和转移氢化外,大多数方法都需要相当苛刻的反应条件才能获得令人满意的脱苄基收率.由于我们对拟肽化学的持续兴趣,我们正在寻找各种 N-苄基和 N,N-二苄基保护的氨基的温和且可能可回收的脱保护方法.如果用于脱苄基化的试
    DOI:10.5012/bkcs.2010.31.03.735

    海关参考信息

    专利信息


    专利号:US-4212828-A
    优先权日:1978-04-14
    标 题:Novel process for asymmetric synthesis of optically active 2-alkanoyl-1,2,3,4-tetrahydro-2-naphthol compounds
    发明人:KOGA KENJI; TERASHIMA SHIRO
    权利人:SUMITOMO CHEMICAL CO
    摘要:A process for asymmetric synthesis of optically active 2-alkanoyl-1,2,3,4-tetrahydro-2-naphthol compounds of the formula: ##STR1## from L-proline or its ester and the following carboxylic acid of the formula: ##STR2## or its reactive derivative through the following intermediary compounds in order: ##STR3##

    专利号:US-4110380-A
    优先权日:1974-05-06
    标题 :Asymmetric synthesis of organic compounds
    发明人:HAJOS ZOLTAN GEORGE; PARRISH DAVID RICHARD
    权利人:HOFFMANN LA ROCHE
    摘要:Optically active organic compounds are prepared starting from optically inactive reactants by means of an optically active agent which influences the course of the reaction. In particular optically active compounds having a 'meso' type carbon atom undergo an intramolecular ring closure in the presence of an optically active agent to yield an optically active product having one additional ring. The present process is particularly useful in the preparation of optically active bicyclic diketones which are important intermediates in the total synthesis of steroids.

    专利号:US-9724682-B2
    优先权日:2013-02-26
    标 题 :Synthesis of acyclic and cyclic amines using iron-catalyzed nitrene group transfer
    发明人:BETLEY THEODORE ALEXANDER; HENNESSY ELISABETH THERESE
    权利人:HARVARD COLLEGE
    摘要:The present invention provides novel synthetic methods for making acyclic secondary amines by reacting an azide with a compound bearing one or more C—H groups, catalyzed by a Fe II -dipyrromethene complex. The acyclic secondary amines are thought to be formed through an intermolecular nitrene transfer. Also provided herein are methods of synthesizing protected (e.g., Boc- or Fmoc-protected) cyclic secondary amines (e.g., 5-, 6-, and 7-membered cyclic secondary amines) by reacting an azide that bears one or more C—H groups, catalyzed by a Fe II -dipyrromethene complex. The protected cyclic secondary amines are thought to be formed through an intramolecular nitrene transfer and may be subsequently deprotected to yield cyclic secondary amines.

    专利号:US-4189447-A
    优先权日:1970-01-21
    标 题:Substituted-hydroxytetrahydroindanones
    发明人:HAJOS ZOLTAN G; PARRISH DAVID R
    权利人:HOFFMANN LA ROCHE
    摘要:Optically active organic compounds are prepared starting from optically inactive reactants by means of an optically active agent which influences the course of the reaction. In particular optically active compounds having a 'meso' type carbon atom undergo an intramolecular ring closure in the presence of an optically active agent to yield an optically active product having one additional ring. The present process is particularly useful in the preparation of optically active bicyclic diketones which are important intermediates in the total synthesis of steroids.

    专利号:US-3975442-A
    优先权日:1970-12-09
    标 题 :2-Alkyl-2-(3-oxoalkyl)-1,3-cyclopentadiones
    发明人:HAJOS ZOLTAN GEORGE; PARRISH DAVID RICHARD
    权利人:HOFFMANN LA ROCHE
    摘要:Optically active organic compounds are prepared starting from optically inactive reactants by means of an optically active agent which influences the course of the reaction. In particular optically active compounds having a 'meso' type carbon atom undergo an intramolecular ring closure in the presence of an optically active agent to yield an optically active product having one additional ring. The present process is particularly useful in the preparation of optically active bicyclic diketones which are important intermediates in the total synthesis of steroids.

    专利号:HU-P0900712-A2
    优先权日:2009-11-13
    标题 :New methods and intermediers for the synthesis of ace-inhibitor

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    品牌试剂参考报价(招募中)

    📌 第三方产品分析报告

    ✅ COA系统入驻 | 共享模式

    主要参考文献

    参考标题:New Highly Diastereoselective Synthesis Of Phosphoramidates. A Route To Chiral MethylP-Nitrophenyl Alkylphosphonates
    作者:Jean-François Cavalier,Frédéric Fotiadu,Robert Verger,Gérard Buono |发布日期:1998.1
    摘要:A New, Efficient And Highly Enantioselective Synthesis Of Methyl P-Nitrophenyl Alkylphosphonates 4 A-C Is Described. Alkylphosphonic Dichloride 1 A-D Reacted Successively With L-Proline Ethyl Ester And P-Nitrophenol To Afford Phosphoramidates 3 A-D In 97% De. Boron Trifluoride Catalysed Methanolysis Gave 4 A-C With 93% Ee. Absolute Configurations Of Compounds 4 C And 3 C Were Established By Correlation With The X-Ray Structure Of Hpl-Colipase-(-)-4 C Complex. 31P Nmr Studies Indicates That Monochloro Phosphoramidates (R P )- And (S P)-2 C Undergo Fast Epimerisation. The Observed Diastereoselectivity In Favour Of (S P)-3 C Results From A Faster Reaction Of (R P)-2 C As Compared To Its Epimer, According To The Curtin-Hammett Principle.

    合成参考文献


    摘要:Börner, A.; Beller, M.; Wünsch, B., Science of Synthesis, (2009) 40, 111.
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