WO2009031526A1 - 光学活性３－キヌクリジノール誘導体の製造方法 - Google Patents

光学活性３－キヌクリジノール誘導体の製造方法 Download PDF

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Publication number
WO2009031526A1
WO2009031526A1 PCT/JP2008/065746 JP2008065746W WO2009031526A1 WO 2009031526 A1 WO2009031526 A1 WO 2009031526A1 JP 2008065746 W JP2008065746 W JP 2008065746W WO 2009031526 A1 WO2009031526 A1 WO 2009031526A1
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WO
WIPO (PCT)
Prior art keywords
optically active
formula
hydrogen atom
ruthenium compound
quinuclidinol
Prior art date
Application number
PCT/JP2008/065746
Other languages
English (en)
French (fr)
Inventor
Takeshi Ohkuma
Noriyoshi Arai
Masaya Akashi
Hirohito Oooka
Tsutomu Inoue
Original Assignee
National University Corporation Hokkaido University
Nippon Soda Co., Ltd.
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 National University Corporation Hokkaido University, Nippon Soda Co., Ltd. filed Critical National University Corporation Hokkaido University
Priority to US12/676,301 priority Critical patent/US8436181B2/en
Priority to KR1020107004462A priority patent/KR101161603B1/ko
Priority to CN200880105289.6A priority patent/CN101796050B/zh
Priority to JP2009531229A priority patent/JP5244113B2/ja
Priority to EP08829356.8A priority patent/EP2186812B1/en
Publication of WO2009031526A1 publication Critical patent/WO2009031526A1/ja
Priority to US13/858,586 priority patent/US8759524B2/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B53/00—Asymmetric syntheses
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/60—Reduction reactions, e.g. hydrogenation
    • B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
    • B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
    • B01J2231/643—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of R2C=O or R2C=NR (R= C, H)
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0261—Complexes comprising ligands with non-tetrahedral chirality
    • B01J2531/0266—Axially chiral or atropisomeric ligands, e.g. bulky biaryls such as donor-substituted binaphthalenes, e.g. "BINAP" or "BINOL"
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/821—Ruthenium

Abstract

　　入手容易なルテニウム化合物を不斉還元触媒として用いて、光学純度の高い光学活性３－キヌクリジノール誘導体を収率よく製造する方法が提供される。この方法は、下記式（I）で表される３－キヌクリジノン誘導体を、式（II）：Ｒｕ（Ｘ）（Ｙ）（Ｐｘ）ｎ［Ｒ１Ｒ２Ｃ＊（ＮＲ３Ｒ４）－Ａ－Ｒ５Ｒ６Ｃ＊（ＮＲ７Ｒ８）］で表されるルテニウム化合物(II)の存在下に、不斉水素化することを特徴とする式（III）で表される光学活性３－キヌクリジノール誘導体の製造方法（式中、Ｒは水素原子、Ｃ７～Ｃ１８アラルキル基等を、Ｘ及びＹは、水素原子、ハロゲン原子等を、Ｐｘはホスフィン配位子を、ｎは１又は２を、Ｒ１～Ｒ８は水素原子、Ｃ１～Ｃ２０アルキル基等を、＊は光学活性な炭素原子を、Ａはエチレン基等をそれぞれ示す。）である。 ［化１］
PCT/JP2008/065746 2007-09-06 2008-09-02 光学活性３－キヌクリジノール誘導体の製造方法 WO2009031526A1 (ja)

Priority Applications (6)

Application Number Priority Date Filing Date Title
US12/676,301 US8436181B2 (en) 2007-09-06 2008-09-02 Production process of optically active 3-quinuclidinol derivative
KR1020107004462A KR101161603B1 (ko) 2007-09-06 2008-09-02 광학 활성 3-퀴누클리디놀 유도체의 제조 방법
CN200880105289.6A CN101796050B (zh) 2007-09-06 2008-09-02 光学活性3-奎核醇衍生物的制造方法
JP2009531229A JP5244113B2 (ja) 2007-09-06 2008-09-02 光学活性３−キヌクリジノール誘導体の製造方法
EP08829356.8A EP2186812B1 (en) 2007-09-06 2008-09-02 Production process of optically active 3-quinuclidinol derivative
US13/858,586 US8759524B2 (en) 2007-09-06 2013-04-08 Production process of optically active 3-quinuclidinol derivative

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2007230973 2007-09-06
JP2007-230973 2007-09-06
JP2008032311 2008-02-13
JP2008-032311 2008-02-13

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US12/676,301 A-371-Of-International US8436181B2 (en) 2007-09-06 2008-09-02 Production process of optically active 3-quinuclidinol derivative
US13/858,586 Continuation US8759524B2 (en) 2007-09-06 2013-04-08 Production process of optically active 3-quinuclidinol derivative

Publications (1)

Publication Number Publication Date
WO2009031526A1 true WO2009031526A1 (ja) 2009-03-12

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PCT/JP2008/065746 WO2009031526A1 (ja) 2007-09-06 2008-09-02 光学活性３－キヌクリジノール誘導体の製造方法

Country Status (6)

Country Link
US (2) US8436181B2 (ja)
EP (1) EP2186812B1 (ja)
JP (1) JP5244113B2 (ja)
KR (1) KR101161603B1 (ja)
CN (1) CN101796050B (ja)
WO (1) WO2009031526A1 (ja)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2639150C2 (ru) * 2013-09-06 2017-12-20 Ниппон Сода Ко., Лтд. Способ получения производного эндо-9-азабицикло[3.3.1]нонан-3-ола
CN105085513B (zh) * 2014-05-20 2017-10-31 中山奕安泰医药科技有限公司 一种制备(r)‑3‑奎宁环醇的方法
CN111454258B (zh) * 2020-05-28 2021-07-20 中山奕安泰医药科技有限公司 索非那新中间体的制备方法

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JP2002284790A (ja) * 2001-01-15 2002-10-03 Nippon Soda Co Ltd ルテニウム化合物、ジアミン配位子および光学活性アルコールの製造方法
JP2003277380A (ja) * 2002-03-20 2003-10-02 Kawaken Fine Chem Co Ltd 光学活性３−キヌクリジノールの製造方法
WO2004007506A1 (ja) * 2002-07-15 2004-01-22 Nippon Soda Co.,Ltd. ルテニウム化合物、ジアミン配位子および光学活性アルコールの製造方法
JP2005306804A (ja) * 2004-04-23 2005-11-04 Takasago Internatl Corp 光学活性３−キヌクリジノールの製造方法
WO2006103756A1 (ja) * 2005-03-30 2006-10-05 Kanto Kagaku Kabushiki Kaisha 光学活性キヌクリジノール類の製造方法

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Also Published As

Publication number Publication date
CN101796050B (zh) 2015-08-12
KR101161603B1 (ko) 2012-07-03
US20100174081A1 (en) 2010-07-08
EP2186812A1 (en) 2010-05-19
CN101796050A (zh) 2010-08-04
JP5244113B2 (ja) 2013-07-24
JPWO2009031526A1 (ja) 2010-12-16
US8436181B2 (en) 2013-05-07
EP2186812B1 (en) 2013-07-03
US8759524B2 (en) 2014-06-24
EP2186812A4 (en) 2011-04-06
KR20100039424A (ko) 2010-04-15
US20130225824A1 (en) 2013-08-29

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