CAS: 57-47-6; (3As,8Ar)-1,3A,8-Trimethyl-1,2,3,3A,8,8A-Hexahydropyrrolo[2,3-B]Indol-5-Yl Methylcarbamate

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CAS号624-83-9 异氰酸甲酯 | CAS号469-22-7 Eseroline | CAS号153109-51-4 (Z)-N-(2-iodo-4... | CAS号153109-54-7 (S,E)-5-methoxy... | CAS号65166-97-4 Esermethole | CAS号139115-75-6 2-iodo-4-methox... | CAS号74-89-5 氨基甲烷 | CAS号18455-27-1 rubreserine | CAS号598-50-5 甲基脲 | CAS号105-40-8 N-甲氨基甲酸乙酯

📜3-甲基-5-苯甲氧基-1H-吲哚置于4-二甲氨基吡啶,甲酸,偶氮二异丁腈,Raney-Nickel W-2,硫酸,硼烷,水,仲丁基锂,三正丁基氢锡,Sodium,三乙胺,间氯过氧苯甲酸,Copper(L) Chloride,锌体系中,用 四氢呋喃,二氯甲烷,N,N-二甲基甲酰胺,甲苯 作为反应溶剂,化学反应 14.85H,反应生成 毒扁豆碱
参考文献:The Enantioselective Synthesis Of (-)-Physostigmine Via Chiral Sulfoxides
标题:The Enantioselective Synthesis Of (-)-Physostigmine Via Chiral Sulfoxides
摘要:The Total Synthesis Of Naturally occurring (-)-Physostigmine Is Described. The Key Element For The Asymmetric Induction Is The Chirality Transfer From Optically Active 2-(Alkylsulfinyl)Indoles To Indoline Butyrolactones Bearing Two Chiral Centers. Novel Features Of This Synthesis Involve The Use Of A New Class Of Sulfoxylating Agents,N-(Alkylsulfinyl)Oxazolidinones,To Prepare The Starting Indolyl Sulfoxides And The Correlation Of The Size Of The Alkyl Group On The Sulfoxide With The Degree Of Asymmetric Induction. The Overall Synthesis Requires A Dozen Steps From Commercially Available 5-(Benzyloxy)Indole.
DOI:10.1021/ja00040A013

专利信息

专利号:US-5840915-A
优先权日:1990-01-22
标题:Process for the enatioselective synthesis of intermediates used
发明人：LEE THOMAS BING KIN; WONG GEORGE SEUNG-KIT
权利人:HOECHST MARION ROUSSEL INC
摘要:A process for the stereoselective synthesis of [R]- and [S]-2,3-dihydro-1,3-dimethyl-2-oxo-1H-indole-3-acetonitriles comprises reacting racemic and 5-alkoxy-substituted (+/-)-1,3-dimethyloxindoles with a halogenated acetonitrile in the presence of a substituted N-benzyl cinchoninium, quinidinium, cinchonidinium, or quininium catalyst. The resulting alkylated oxindoles can be converted to primary amines by catalytic reduction in the presence of hydrogen gas. One of the primary amines, such as enantiomers of 3-(2-aminoethyl)-1,3-dihydro-1,3-dimethyl-5-methoxy-2H-indol-2-one, can be enriched by contact with a chiral tartaric acid in an amount sufficient to preferentially precipitate a salt of the chiral acid and one of the enantiomers. The product can be used in the synthesis of stereospecific forms of physostigmine and related compounds having pharmaceutical activity.

专利号:US-5274117-A
优先权日:1990-01-22
标 题:Process for the enantioselective synthesis of intermediates used in the preparation of physostigmine
发明人：LEE THOMAS BING KIN DR; WONG GEORGE S K
权利人:HOECHST ROUSSEL PHARMA
摘要:A process for the stereoselective synthesis of [R]- and [S]-2,3-dihydro-1,3-dimethyl-2-oxo-1H-indole-3-acetonitriles comprises reacting racemic and 5-alkoxy-substituted (+/-)-1,3-dimethyloxindoles with a halogenated acetonitrile in the presence of a substituted N-benzyl cinchoninium, quinidinium, cinchonidinium, or quininium catalyst. The resulting alkylated oxindoles can be converted to primary amines by catalytic reduction in the presence of hydrogen gas. One of the primary amines, such as enantiomers of 3-(2-aminoethyl)-1,3-dihydro-1,3-dimethyl-5-methoxy-2H-indol-2-one, can be enriched by contact with a chiral tartaric acid in an amount sufficient to preferentially precipitate a salt of the chiral acid and one of the enantiomers. The product can be used in the synthesis of stereospecific forms of physostigmine and related compounds having pharmaceutical activity.

专利号:EP-0438796-B1
优先权日:1990-01-22
标题:Process for the enantioselection synthesis of alkylated oxindoles used as intermediates in the preparation of physostigmine
发明人：LEE THOMAS BING KIN DR; WONG GEORGE S K
权利人:HOECHST MARION ROUSSEL INC
摘要:A process for the stereoselective synthesis of [R]- and [S]-2,3-dihydro-1,3-dimethyl-2-oxo-1H-indole-3-acetonitriles comprises reacting racemic and 5-alkoxy-substituted (+/-)-1,3-dimethyloxindoles with a halogenated acetonitrile in the presence of a substituted N-benzyl cinchoninium, quinidinium, cinchonidinium, or quininium catalyst. The resulting alkylated oxindoles can be converted to primary amines by catalytic reduction in the presence of hydrogen gas. One of the primary amines, such as enantiomers of 3-(2-aminoethyl)-1,3-dihydro-1,3-dimethyl-5-methoxy-2H-indol-2-one, can be enriched by contact with a chiral tartaric acid in an amount sufficient to preferentially precipitate a salt of the chiral acid and one of the enantiomers. The product can be used in the synthesis of stereospecific forms of physostigmine and related compounds having pharmaceutical activity.

专利号:US-6271379-B1
优先权日:2000-03-08
标题:Intermediates useful for the synthesis of huperzine A
发明人：TUECKMANTEL WERNER; KOZIKOWSKI ALAN P
权利人:UNIV GEORGETOWN
摘要:Intermediates useful for the synthesis of huperzine A represented by the structures below, n and methods for their synthesis, wherein: n R 1 is lower alkyl, benzyl, or substituted benzyl; n X is a suitable leaving group; n Y is an electron withdrawing group that can subsequently be converted into an amino group; n one broken line is present as a carbon—carbon bond and the other broken line is absent, where the broken line forms an unconjugated carbon—carbon double bond, which double bond may be endocyclic whereby n is 3 or the double bond may be exocyclic whereby n is 2.

专利号:US-2003083352-A1
优先权日:2000-07-31
标 题 :Synthesis of imidazole intermediates
发明人：HELAL CHRISTOPHER J
权利人:PFIZER
摘要:The invention provides a method for synthesis of compounds of formula n n n wherein R 1 and R 19 are as defined. Compounds of formula 12 are useful as intermediates for synthesizing compounds having pharmacological activity inhibiting cdk5, cdk2, and GSK-3.

专利号:US-9315483-B2
优先权日:2007-09-13
标题 :Synthesis of deuterated catechols and benzo[D][1,3]dioxoles and derivatives thereof
发明人：JONES ANDREW D; ZELLE ROBERT E; SILVERMAN I ROBERT
权利人:CONCERT PHARMACEUTICALS INC
摘要:The present invention provides a convenient and efficient process for the synthesis of d 2 -benzo[d][1,3]dioxoles.