CAS: 86953-79-9; Tert-Butyl Pyrrolidine-1-Carboxylate

该化合物是具有酯功能组特征的有机化合物,其特点是:有5个含氮的乙型环,以及附于碳箱状细胞的三丁基(1,1-二甲基乙基),该化合物一般没有色素,可粉色黄色液体,有独特的气味;在标准条件下,该化合物溶于有机溶剂,具有中等稳定性;该阳性环的存在表明在制药和农用化学品中的潜在用途,因为这种结构的化合物往往展示出有趣的生物活动.此外,三丁基化合物可影响该化合物的性能和反应性,使其成为合成有机化学的一个主题.在处理和储存时,应参考安全数据,如同任何化学物质,以确保采取适当的防范措施.

结构式图片

相似化合物

29897-82-3 3760-54-1 25070-74-0

物理性质

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合成工艺路线路线简述

  • 合成目标产物 1-Boc-Pyrrolidine 主要起始原料 Pyrrolidine And Di-Tert-Butyl Dicarbonate
  • 2055648-50-3 = 86953-79-9
    反应条件:1.1 Reagents: Triethylamine Solvents: Ethyl Acetate; 10 Min,Rt
    标题:A Novel Use Of Boc-Oxyma As Reagent For Tert-Butoxycarbonylation Of Amines And Amino Acid Esters
    作者:Robert,Alice R.; Et Al
    参考文献:Chemical Data Collections 日期:2020 卷标:30]

    24424-99-5 = 86953-79-9
    反应条件:1.1 Reagents: 4-(Dimethylamino)Pyridine Solvents: Dichloromethane; 0 °C; 10 Min,0 °C; 0 °C -> Rt; 24 H,Rt
    标题:Dual Benzophenone/copper-Photocatalyzed Giese-Type Alkylation Of C(Sp3)-H Bonds
    作者:Abadie,Baptiste; Et Al
    参考文献:Chemistry - A European Journal 日期:2019 卷标:25(70) 页码:16120-16127]

    24424-99-5 = 86953-79-9
    反应条件:1.1 Catalysts: Amberlyst 15 Solvents: Ethanol; < 1 Min,Rt
    标题:An Efficient And Highly Chemoselective N-Boc Protection Of Amines,Amino Acids,And Peptides Under Heterogeneous Conditions
    作者:Jahani,Fatemeh; Et Al
    参考文献:Monatshefte Fuer Chemie 日期:2011 卷标:142(10) 页码:1035-1043]

    151259-38-0 = 86953-79-9
    反应条件:1.1 Catalysts: Grubbs' Catalyst Solvents: Dichloromethane; Overnight,Rt
    标题:Iron- And Cobalt-Catalyzed Arylation Of Azetidines,Pyrrolidines,And Piperidines With Grignard Reagents
    作者:Barre,Baptiste; Et Al
    参考文献:Organic Letters 日期:2014 卷标:16(23) 页码:6160-6163]

    = 86953-79-9
    反应条件:1.1 Reagents: Oxygen Catalysts: Cuprous Iodide,Gold Trichloride; 0.1 Mpa,Rt; 24 H,0.4 Mpa,Rt
    标题:Sustainable Route Toward N-Boc Amines: Aucl3/cui-Catalyzed N-Tert-Butyloxycarbonylation Of Amines At Room Temperature
    作者:Cao,Yanwei; Et Al
    参考文献:Chemsuschem 日期:2022 卷标:15(4)]

    5176-27-2 = 86953-79-9
    反应条件:1.1 Reagents: Hydrogen Catalysts: Triphenylphosphine,[(1,2,5,6-η)-1,5-Cyclooctadiene](2,4-Pentanedionato-Ko2,Ko4)Rhodium Solvents: Isopropanol
    标题:Hydrogenation Of Five-Membered Heteroaromatic Compounds Catalyzed By A Rhodium-Phosphine Complex
    作者:Kuwano,Ryoichi; Et Al
    参考文献:Chemistry Letters 日期:2000 卷标:(4) 页码:428-429]

    1289386-88-4 = 86953-79-9
    反应条件:1.1 Reagents: Cesium Carbonate,Cesium Formate Catalysts: 3,5-Bis(1,1-Dimethylethyl)[1,1′-Biphenyl]-4-Ol,Cysteine Solvents: Dimethylformamide; 4 H,Rt
    标题:Phenolate Anion-Catalyzed Direct Activation Of Inert Alkyl Chlorides Driven By Visible Light
    作者:Wei,Delian; Et Al
    参考文献:Organic Chemistry Frontiers 日期:2021 卷标:8(22) 页码:6364-6370]

    170491-63-1 = 86953-79-9
    反应条件:1.1 Reagents: 2,4,6-Trimethylpyridine Catalysts: Tetrabutylammonium Chloride,Iron Chloride (Fecl3),Bis[2,4,6-Tris(1-Methylethyl)Phenyl] Disulfide Solvents: 1,2-Dichloroethane; 48 H,Rt
    标题:Iron-Catalyzed C-C Single-Bond Cleavage Of Alcohols
    作者:Liu,Wei; Et Al
    参考文献:Organic Letters 日期:2021 卷标:23(21) 页码:8413-8418]

    15761-39-4 = 86953-79-9
    反应条件:1.1 Reagents: Phenanthrene,1-Dodecanethiol,1,4-Dicyanobenzene,Sodium Hydroxide Solvents: Acetonitrile,Water; 6 H
    标题:Decarboxylative Reduction Of Free Aliphatic Carboxylic Acids By Photogenerated Cation Radical
    作者:Yoshimi,Yasuharu; Et Al
    参考文献:Chemical Communications (Cambridge 日期:2007 卷标:(48) 页码:5244-5246]

    24608-52-4 = 86953-79-9
    反应条件:1.1 Reagents: Triethylamine Solvents: Dichloromethane; 0 °C; 16 H,Rt
    标题:Copper Catalyzed Late-Stage C(Sp3)-H Functionalization Of Nitrogen Heterocycles
    作者:Chang,Zhe; Et Al
    参考文献:Nature Communications 日期:2021 卷标:12(1)]

    = 86953-79-9 [标题:Reaction Conditions
    标题:Stereoselective Cross-Coupling Of Chiral Amino Acid Chlorides And Hydrocarbons Through Mechanistically Controlled Ni/ir Photoredox Catalysis
    作者:Lee,Geun Seok; Et Al
    参考文献:Nature Communications 日期:2022 卷标:13(1)]

    = 86953-79-9
    反应条件:1.1 Reagents: Thiophenol Catalysts: Iridium(1+),[4,4′-Bis(1,1-Dimethylethyl)-2,2′-Bipyridine-Kn1,Kn1′]Bis[3,5-Diflu... Solvents: Methanol,Acetone; 16 H,Rt
    标题:Catalytic Protodeboronation Of Pinacol Boronic Esters: Formal Anti-Markovnikov Hydromethylation Of Alkenes
    作者:Clausen,Florian; Et Al
    参考文献:Chemical Science 日期:2019 卷标:10(24) 页码:6210-6214]

    73286-70-1 = 86953-79-9
    反应条件:1.1 Reagents: Water,Diboronic Acid Catalysts: Palladium Solvents: Dichloromethane; 60 H,Rt
    标题:Tetrahydroxydiboron-Mediated Palladium-Catalyzed Transfer Hydrogenation And Deuteriation Of Alkenes And Alkynes Using Water As The Stoichiometric H Or D Atom Donor
    作者:Cummings,Steven P.; Et Al
    参考文献:Journal Of The American Chemical Society 日期:2016 卷标:138(19) 页码:6107-6110]

    73286-70-1 = 86953-79-9
    反应条件:1.1 Reagents: Water,Pinacolborane Catalysts: Palladium Diacetate Solvents: Dichloromethane; 12 H,25 °C
    标题:Generalized Chemoselective Transfer Hydrogenation/hydrodeuteration
    作者:Wang,Yong; Et Al
    参考文献:Advanced Synthesis & Catalysis 日期:2020 卷标:362(19) 页码:4119-4129]

    149682-81-5 = 86953-79-9
    反应条件:1.1 Reagents: Phenyllithium Solvents: Diethyl Ether,Butyl Ether; Rt -> 0 °C; 30 Min,0 °C -> Rt1.2 Reagents: Thiophenol Catalysts: Iridium(1+),[4,4′-Bis(1,1-Dimethylethyl)-2,2′-Bipyridine-Kn1,Kn1′]Bis[3,5-Diflu... Solvents: Methanol,Acetone; 16 H,Rt
    标题:Catalytic Protodeboronation Of Pinacol Boronic Esters: Formal Anti-Markovnikov Hydromethylation Of Alkenes
    作者:Clausen,Florian; Et Al
    参考文献:Chemical Science 日期:2019 卷标:10(24) 页码:6210-6214]

    59433-50-0 = 86953-79-9
    反应条件:1.1 Reagents: Sodium Carbonate Catalysts: Bis(2-Pyridylmethyl)Amine,Ferric Nitrate,Bis[2,4,6-Tris(1-Methylethyl)Phenyl] Disulfide Solvents: 1,2-Dichloroethane,Water; 20 H
    标题:Chemoselective Decarboxylative Protonation Enabled By Cooperative Earth-Abundant Element Catalysis
    作者:Lu,Yen-Chu; Et Al
    参考文献:Angewandte Chemie 日期:2023 卷标:62(3)]

    170491-63-1 = 86953-79-9
    反应条件:1.1 Catalysts: Tetrabutylammonium Chloride,9,10-Diphenylanthracene,Cerium Trichloride,Bis[2,4,6-Tris(1-Methylethyl)Phenyl] Disulfide Solvents: Acetonitrile; 24 H,Rt
    标题:Dehydroxymethylation Of Alcohols Enabled By Cerium Photocatalysis
    作者:Zhang,Kaining; Et Al
    参考文献:Journal Of The American Chemical Society 日期:2019 卷标:141(26) 页码:10556-10564]

    236101-14-7 = 86953-79-9
    反应条件:1.1 Reagents: Lithium Hydroxide Solvents: Tetrahydrofuran,Water1.2 Reagents: Potassium Tert-Butoxide Solvents: Dimethylformamide
    标题:N-Boc And N-Cbz Ethyl Oxamates: New Gabriel Reagents
    作者:Berree,Fabienne; Et Al
    参考文献:Synthetic Communications 日期:1999 卷标:29(15) 页码:2685-2693]

    91837-45-5 = 86953-79-9
    反应条件:1.1 Reagents: Tetrabutylammonium Tetrafluoroborate,Dithiothreitol Solvents: 1,2-Dimethoxyethane; 4 H,20 °C
    标题:Catalyst-Free Decarboxylation Of Carboxylic Acids And Deoxygenation Of Alcohols By Electro-Induced Radical Formation
    作者:Chen,Xiaoping; Et Al
    参考文献:Chemistry - A European Journal 日期:2020 卷标:26(15) 页码:3226-3230]

    117625-90-8 = 86953-79-9
    反应条件:1.1 Catalysts: 1,3-Bis(Diphenylphosphino)Propane,Di-μ-Chlorobis[(1,2,5,6-η)-1,5-Cyclooctadiene]Dirhodium Solvents: Xylene; 18 H,160 °C
    标题:Ligand Enabled None-Oxidative Decarbonylation Of Aliphatic Aldehydes
    作者:Li,Bo; Et Al
    参考文献:Chinese Chemical Letters 日期:2023 卷标:34(7)]

    59378-75-5 = 86953-79-9
    反应条件:1.1 Reagents: 2,4,6-Trimethylpyridine,Ammonium Persulfate Solvents: Dmso-D6; 16 H,40 °C
    标题:Direct Hydrodecarboxylation Of Aliphatic Carboxylic Acids: Metal- And Light-Free
    作者:Mclean,Euan B.; Et Al
    参考文献:Organic Letters 日期:2022 卷标:24(2) 页码:686-691
📜1-Boc-吡咯烷-3-甲酸置于2,4,6-三甲基吡啶,Ammonium Peroxydisulfate体系中,用 氘代二甲亚砜 作为反应溶剂,化学反应 16.0H,以50%的收率获得产物1-Boc-四氢吡咯
参考文献:脂肪族羧酸的直接加氢脱羧:无金属和无光
标题:脂肪族羧酸的直接加氢脱羧:无金属和无光
摘要:已经开发了一种用于脂肪族羧酸直接加氢脱羧的温和且廉价的方法.该反应不需要金属,光或催化剂,使该协议操作简单,易于扩展且更具可持续性.至关重要的是,在大多数情况下不需要额外的 H 原子源,同时观测到广泛的底物范围和官能团耐受性.
DOI:10.1021/acs.Orglett.1C04079

海关参考信息

专利信息


专利号:US-2012302756-A1
优先权日:2010-02-19
标 题 :Process for synthesis of 2-substituted pyrrolidines and piperadines
发明人：LELETI RAJENDER REDDY; LIU YUGANG; PRASHAD MAHAVIR
权利人:LELETI RAJENDER REDDY; LIU YUGANG; PRASHAD MAHAVIR
摘要:The present invention provides a highly efficient, versatile one-step process for asymmetric synthesis of either diastereomer of 2-substituted pyrrolidines from a single starting material with excellent yields and high diastereoselectivety. Also provided is a method for the asymmetric synthesis of both diastereomers of 2-substituted piperidines with good yields and excellent diastereoselectivety. Diasteroselectivity is controlled effectively by choice of reducing agent.

专利号:US-6025502-A
优先权日:1999-03-19
标题:Enantopselective synthesis of methyl phenidate
发明人：WINKLER JEFFREY DAVID; AXTEN JEFFREY M; KRIM LORI
权利人:UNIV PENNSYLVANIA
摘要:The invention relates to an enantioselective method of making methylphenidate and derivatives thereof. The method involves use of a rhodium catalyst, and selectively produces the D-enantiomer of the methylphenidate derivative in excess of the L-enantiomer thereof. Furthermore, the method selectively produces the threo-diastereomer in excess of the erythro-diastereomer. The method is thus suitable for synthesis of D-threo-methylphenidate (the biologically active form of this compound) and derivatives thereof.

专利号:US-2012053350-A1
优先权日:2009-04-30
标题 :Preparation of alkyl esters of n-protected oxo-azacycloalkylcarboxylic acids
发明人：MANGION IAN; HUFFMAN MARK A; RUCK REBECCA T; LYNCH JOSEPH; CHUNG JOHN Y L; MARCUNE BENJAMIN
权利人:MANGION IAN; HUFFMAN MARK A; RUCK REBECCA T; LYNCH JOSEPH; CHUNG JOHN Y L; MARCUNE BENJAMIN
摘要:A process for the preparation of alkyl esters of N-protected oxo-azacycloalkylcarboxylic acids of Formula III: comprises contacting a ketosulfoxonium ylide of Formula II: with an iridium catalyst to obtain Compound III, wherein P G1 is an amine protective group; k is 0, 1, or 2; and R U , R 1 , R 2 , and R 3 are defined herein. An embodiment of the process further com rises contacting a compound of Formula I: with a sulfoxonium halide of formula (R U ) 3 S(O)Z, wherein Z is halide, in the presence of a strong base to obtain Compound II. Additional embodiments add a series of process steps leading to the synthesis of 7-oxo-1,6-diazabicyclo[3.2.1]octanes suitable for use as β-lactamase inhibitors.

专利号:US-2004110228-A1
优先权日:2002-04-01
标 题:Combinatorial organic synthesis of unique biologically active compounds
发明人：MCALPINE SHELLI R; TAYLOR RACHEL E; BOLLA MEGAN L; SEGALL ANCA M
摘要:The invention provides a method for making a combinatorial library of cyclic compounds, such as Holliday junction-trapping compounds, comprising the steps of (a) obtaining a plurality of trimers according to the generic structure X 1- X 2- X 3 , wherein X 1 , X 2 and X 3 can be independently any naturally or nonnaturally occurring amino acids or peptidomimetics thereof; (b) optionally coupling a spacer S to the trimer at either end; (c) cyclizing two trimers or trimer-spacer conjugates in a head-to-tail orientation; thereby obtaining a combinatorial library of compounds, wherein the library does not include an unmodifed or naturally occurring Holliday Junction-trapping compounds. The invention additionally provides methods macrocyclic compounds that are synergimycin derivatives.

专利号:US-9676783-B2
优先权日:2008-10-22
标 题:Method of treatment using substituted pyrazolo[1,5-A] pyrimidine compounds
发明人：HAAS JULIA; ANDREWS STEVEN W; JIANG YUTONG; ZHANG GAN
权利人:ARRAY BIOPHARMA INC
摘要:Compounds useful in the synthesis of compounds for treating pain, cancer, inflammation, neurodegenerative disease or Typanosoma cruzi infection in a mammal.

专利号:US-7402670-B2
优先权日:2004-09-30
标 题:Synthesis by chiral diamine-mediated asymmetric alkylation
发明人：DENG XIAOHU; MANI NEELAKANDHA
权利人:JANSSEN PHARMACEUTICA NV
摘要:Chiral synthesis from an achiral starting material by chiral diamine-mediated, such as sparteine-mediated, intermolecular asymmetric alkylation with a strained cyclic ether in the presence of a Lewis acid.

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主要参考文献

[参考文献]: Graeme Barker, Et Al. Enantioselective, Palladium-Catalyzed α-Arylation Of N-Boc Pyrrolidine: In Situ React Ir Spectroscopic Monitoring, Scope, And Synthetic Applications. J Org Chem. 2011 Aug 5;76(15):5936-53.

合成参考文献


参考文献:10.1021/jo200991q
摘要:Jentzsch KI, Min T, Etcheson JI, Fettinger JC, Franz AK. Silyl fluoride electrophiles for the enantioselective synthesis of silylated pyrrolidine catalysts. J Org Chem. 2011 Sep 02;76(17):7065–75. doi: 10.1021/jo200991q.
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