EA200801673A1 - Асимметрическое алкилирование карбонильных групп - Google Patents

Асимметрическое алкилирование карбонильных групп

Info

Publication number
EA200801673A1
EA200801673A1 EA200801673A EA200801673A EA200801673A1 EA 200801673 A1 EA200801673 A1 EA 200801673A1 EA 200801673 A EA200801673 A EA 200801673A EA 200801673 A EA200801673 A EA 200801673A EA 200801673 A1 EA200801673 A1 EA 200801673A1
Authority
EA
Eurasian Patent Office
Prior art keywords
boric
boronic acid
alkylation
carbonyl group
compound containing
Prior art date
Application number
EA200801673A
Other languages
English (en)
Other versions
EA016650B1 (ru
Inventor
Мартин Альберт
Хуберт Штурм
Андреас Бергер
Петер Креммингер
Original Assignee
Сандоз Аг
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Сандоз Аг filed Critical Сандоз Аг
Publication of EA200801673A1 publication Critical patent/EA200801673A1/ru
Publication of EA016650B1 publication Critical patent/EA016650B1/ru

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/56—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and doubly-bound oxygen atoms bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
    • C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
    • C07C215/30—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings containing hydroxy groups and carbon atoms of six-membered aromatic rings bound to the same carbon atom of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
    • C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
    • C07C215/30—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings containing hydroxy groups and carbon atoms of six-membered aromatic rings bound to the same carbon atom of the carbon skeleton
    • C07C215/32—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings containing hydroxy groups and carbon atoms of six-membered aromatic rings bound to the same carbon atom of the carbon skeleton containing hydroxy groups and carbon atoms of two six-membered aromatic rings bound to the same carbon atom of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/53—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

В заявке описаны способы и промежуточные продукты для стереоселективного алкилирования карбонильных групп. Настоящее изобретение, в частности, позволяет стереоселективно синтезировать антидепрессивное лекарственное средство эсциталопрам. Согласно изобретению было установлено, что производные борной или бороновой кислоты являются подходящими мостиковыми элементами для присоединения хиральной группы к соединению, содержащему алкилируемую карбонильную группу. Таким образом, указанные бораты и боронаты применимы в способе асимметрического алкилирования карбонильной группы в соединении, содержащем карбонильную группу и связывающую группу, способную взаимодействовать с производным борной или бороновой кислоты. Асимметрическое алкилирование можно провести путем смешивания соединения, содержащего алкилируемую карбонильную группу и связывающую группу, способную взаимодействовать с производным борной или бороновой кислоты с производным борной или бороновой кислоты, прибавления хирального спирта и прибавления металлорганического соединения. После реакции алкилирования борат и боронат можно легко удалить с помощью гидролиза.
EA200801673A 2006-01-23 2007-01-22 Способ асимметрического алкилирования карбонильной группы EA016650B1 (ru)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB0601286.8A GB0601286D0 (en) 2006-01-23 2006-01-23 Asymmetric synthesis
PCT/EP2007/000516 WO2007082771A1 (en) 2006-01-23 2007-01-22 Carbonyl asymmetric alkylation

Publications (2)

Publication Number Publication Date
EA200801673A1 true EA200801673A1 (ru) 2009-02-27
EA016650B1 EA016650B1 (ru) 2012-06-29

Family

ID=36010766

Family Applications (1)

Application Number Title Priority Date Filing Date
EA200801673A EA016650B1 (ru) 2006-01-23 2007-01-22 Способ асимметрического алкилирования карбонильной группы

Country Status (19)

Country Link
US (1) US8288569B2 (ru)
EP (1) EP1966127B1 (ru)
JP (1) JP5081163B2 (ru)
KR (1) KR101379154B1 (ru)
CN (1) CN101460448B (ru)
AT (1) ATE504558T1 (ru)
AU (1) AU2007207103B2 (ru)
BR (1) BRPI0706735B1 (ru)
CA (1) CA2636256C (ru)
DE (1) DE602007013690D1 (ru)
EA (1) EA016650B1 (ru)
ES (1) ES2364502T3 (ru)
GB (1) GB0601286D0 (ru)
HR (1) HRP20110492T1 (ru)
IL (1) IL192628A (ru)
PL (1) PL1966127T3 (ru)
SI (1) SI1966127T1 (ru)
TW (1) TWI387577B (ru)
WO (1) WO2007082771A1 (ru)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2667909C2 (ru) * 2012-03-14 2018-09-25 Мерк Шарп И Доум Корп. Бисчетвертичные соли алкалоида хинного дерева в качестве асимметрических межфазных катализаторов

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110130591A1 (en) * 2009-06-03 2011-06-02 Boehringer Ingelheim International Gmbh Steroselective synthesis of certain trifluoromethyl-substituted alcohols
PT3013801T (pt) * 2013-06-26 2018-11-16 Syngenta Participations Ag Processo para a preparação estereosseletiva de uma pirazol-carboxamida
CN107074750B (zh) * 2014-11-14 2022-03-25 浙江华海药业股份有限公司 一种拆分西酞普兰中间体5-氰二醇的方法
KR20160109083A (ko) 2015-03-09 2016-09-21 엔팩토리주식회사 휴대용 앱세서리를 이용한 공기품질 정보제공 시스템 및 방법
US10111356B2 (en) 2016-03-31 2018-10-23 Oracle International Corporation System for electrical connection of printed circuit boards and backplanes in server enclosure
CN106892837A (zh) * 2017-03-23 2017-06-27 浙江师范大学 4‑[4‑(二甲氨基)‑1‑(4‑氟苯基)‑1‑羟丁基]‑3‑羟甲基苯腈的合成
CN108947869A (zh) * 2017-05-25 2018-12-07 万全万特制药江苏有限公司 一种艾司西酞普兰工艺杂质的制备方法
CN108640855A (zh) * 2018-06-11 2018-10-12 中南林业科技大学 一种依地普仑中间体的合成方法及其中间体
CN108640856B (zh) * 2018-06-11 2021-06-25 淮阴工学院 一种依地普仑中间体的不对称合成方法及其中间体

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1526331A (en) 1976-01-14 1978-09-27 Kefalas As Phthalanes
GB8419963D0 (en) * 1984-08-06 1984-09-12 Lundbeck & Co As H Intermediate compound and method
GB8814057D0 (en) 1988-06-14 1988-07-20 Lundbeck & Co As H New enantiomers & their isolation
UA62985C2 (en) 1997-11-10 2004-01-15 Lunnbeck As H A method for the preparation of citalopram
ES2229774T3 (es) * 1999-10-25 2005-04-16 H. Lundbeck A/S Metodo para la preparacion de citalopram.
FR2805812A1 (fr) 2000-02-24 2001-09-07 Lundbeck & Co As H Procede de preparation du citalopram
IES20010157A2 (en) 2000-03-03 2002-03-06 Lundbeck & Co As H Method for the preparation of citalopram
JP2003527387A (ja) 2000-03-13 2003-09-16 ハー・ルンドベック・アクチエゼルスカベット シタロプラムの製造方法
AR034759A1 (es) 2001-07-13 2004-03-17 Lundbeck & Co As H Metodo para la preparacion de escitalopram
PT1414435E (pt) 2001-07-31 2005-05-31 Lundbeck & Co As H Composicao cristalina contendo escitalopram
DE60108105T2 (de) * 2001-08-02 2005-12-08 Infosint Sa Verfahren zur Herstellung von 5-substituierten Isobenzofuranen
PE20040991A1 (es) 2002-08-12 2004-12-27 Lundbeck & Co As H Separacion de intermediarios para la preparacion de escitalopram
WO2005066185A1 (en) 2004-01-12 2005-07-21 Jubilant Organosys Limited Process for preparing 5-substituted -1-(4-fluorophenyl) -1,3-dihydroisobenzofurans
JP2005247710A (ja) * 2004-03-01 2005-09-15 Sumitomo Chemical Co Ltd 光学活性シタロプラムの製造方法、その中間体およびその製造方法

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2667909C2 (ru) * 2012-03-14 2018-09-25 Мерк Шарп И Доум Корп. Бисчетвертичные соли алкалоида хинного дерева в качестве асимметрических межфазных катализаторов

Also Published As

Publication number Publication date
CA2636256C (en) 2014-04-29
TW200800858A (en) 2008-01-01
IL192628A (en) 2013-04-30
IL192628A0 (en) 2009-02-11
US20110009648A1 (en) 2011-01-13
TWI387577B (zh) 2013-03-01
SI1966127T1 (sl) 2011-08-31
KR20080090444A (ko) 2008-10-08
CN101460448A (zh) 2009-06-17
ES2364502T3 (es) 2011-09-05
US8288569B2 (en) 2012-10-16
PL1966127T3 (pl) 2011-10-31
EA016650B1 (ru) 2012-06-29
DE602007013690D1 (de) 2011-05-19
EP1966127B1 (en) 2011-04-06
JP5081163B2 (ja) 2012-11-21
AU2007207103B2 (en) 2011-01-06
ATE504558T1 (de) 2011-04-15
CN101460448B (zh) 2013-05-15
HRP20110492T1 (hr) 2011-07-31
KR101379154B1 (ko) 2014-04-11
BRPI0706735B1 (pt) 2016-11-22
BRPI0706735A2 (pt) 2011-04-05
EP1966127A1 (en) 2008-09-10
CA2636256A1 (en) 2007-07-26
GB0601286D0 (en) 2006-03-01
JP2009523749A (ja) 2009-06-25
WO2007082771A1 (en) 2007-07-26
AU2007207103A1 (en) 2007-07-26

Similar Documents

Publication Publication Date Title
ATE504558T1 (de) Asymmetrische carbonylalkylierung
CY1124753T1 (el) Συνθεση ενωσεων βορονικων εστερων και οξεων
AR075291A1 (es) Proceso para la preparcion de derivados de l-alanina protegidos
EA201201179A1 (ru) Способ получения изоксазолиновых производных
BRPI0712272A2 (pt) Processos para a fabricação de pelo menos um isoocteno, de produtos de reação, de pelo menos um isooctano e de pelos menos um isooctanol
BRPI0816911A8 (pt) Processo para preparação de 4-aminobut-2-enolidas
CL2012001457A1 (es) Proceso para obtener marcado de polímero de cristal líquido que comprende, aplicar composición precursora a sustrato, calentar, aplicar segunda composición precursora, calentar, curar y polimerizar; marcado de polimero con primera y segunda composicion precursora que comprende compuesto dopante quiral, y sustrato.
CL2008003041A1 (es) Compuestos derivados de acido boronico, inhibidores de proteasoma; composicion farmaceutica que comprende a dicho compuesto; y uso del compuesto para el tratamiento del cancer.
ATE477234T1 (de) Synthese von phenolischen estern von hydroxymethylphenolen
TW200612959A (en) Method for preparing hydroxamic acids
BR112013003059A2 (pt) processo para preparar composto 2-hidroxifenil alquenil benzotriazol e processo para preparar compostos siloxano contendo função 2-hidroxifenil benzotriazol
WO2009135598A8 (en) Process for preparing substituted biphenylanilides
CL2010001441A1 (es) Proceso para la preparacion de derivados de 2-amino tiazolonas sustituidas utilizando derivados de efedrina como base quiral.
MY155300A (en) Preparation of saturated imidazolinium salts and related compounds
MX2013000294A (es) Intermedios y procedimiento de preparación de un inhibidor específico de la trombina.
EA200900008A1 (ru) Новые хиральные промежуточные продукты, способ их получения и их применение в производстве толтеродина, фезотеродина или их активных метаболитов
BR112012019866A8 (pt) Composto, uso do mesmo, composição farmacêutica, e, processo para preparar um composto
MX2010009926A (es) Nuevo proceso para la preparacion de derivados de acido ciclohexancarboxilico.
GB201104203D0 (en) Chemical process
GB2497841A (en) Subsea hydrocarbon production system
BRPI0914807A2 (pt) Processo para a preparação de compostos inibidores de rho-quinase
MA32698B1 (fr) Procede de preparation du 1,6:2,3-dianhydro-beta-d-mannopyranose
ATE461194T1 (de) Chemisches verfahren
CR20110178A (es) Proceso para la preparación de etanodinitrilo
UA86549C2 (en) 1-(aminomethyl)-2,2,2-trifluoroethyl phosphonic acid

Legal Events

Date Code Title Description
MM4A Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s)

Designated state(s): AM AZ BY KZ KG MD TJ TM

MM4A Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s)

Designated state(s): RU