CN103168019B - 双环[2.2.2]辛-2-酮化合物的制备 - Google Patents

双环[2.2.2]辛-2-酮化合物的制备 Download PDF

Info

Publication number
CN103168019B
CN103168019B CN201180050144.2A CN201180050144A CN103168019B CN 103168019 B CN103168019 B CN 103168019B CN 201180050144 A CN201180050144 A CN 201180050144A CN 103168019 B CN103168019 B CN 103168019B
Authority
CN
China
Prior art keywords
compound
formula
phenyl
group
ester
Prior art date
Legal status (The legal status 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 status listed.)
Expired - Fee Related
Application number
CN201180050144.2A
Other languages
English (en)
Chinese (zh)
Other versions
CN103168019A (zh
Inventor
斯黛芬·阿波勒
雅克-亚丽克西斯·富内尔
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Actelion Pharmaceuticals Ltd
Original Assignee
Actelion Pharmaceuticals 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 Actelion Pharmaceuticals Ltd filed Critical Actelion Pharmaceuticals Ltd
Publication of CN103168019A publication Critical patent/CN103168019A/zh
Application granted granted Critical
Publication of CN103168019B publication Critical patent/CN103168019B/zh
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/385—Saturated compounds containing a keto group being part of a ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C07C309/66—Methanesulfonates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • C07C45/66—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/313—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of doubly bound oxygen containing functional groups, e.g. carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/44—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing eight carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
CN201180050144.2A 2010-10-20 2011-10-19 双环[2.2.2]辛-2-酮化合物的制备 Expired - Fee Related CN103168019B (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IBPCT/IB2010/054747 2010-10-20
IB2010054747 2010-10-20
PCT/IB2011/054660 WO2012052939A2 (en) 2010-10-20 2011-10-19 Preparation of bicyclo[2.2.2]octan-2-one compounds

Publications (2)

Publication Number Publication Date
CN103168019A CN103168019A (zh) 2013-06-19
CN103168019B true CN103168019B (zh) 2015-05-27

Family

ID=45757740

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201180050144.2A Expired - Fee Related CN103168019B (zh) 2010-10-20 2011-10-19 双环[2.2.2]辛-2-酮化合物的制备

Country Status (13)

Country Link
US (1) US9296673B2 (cg-RX-API-DMAC7.html)
EP (1) EP2630111B1 (cg-RX-API-DMAC7.html)
JP (1) JP5909237B2 (cg-RX-API-DMAC7.html)
KR (1) KR101876594B1 (cg-RX-API-DMAC7.html)
CN (1) CN103168019B (cg-RX-API-DMAC7.html)
CA (1) CA2813131C (cg-RX-API-DMAC7.html)
DK (1) DK2630111T3 (cg-RX-API-DMAC7.html)
ES (1) ES2536897T3 (cg-RX-API-DMAC7.html)
HU (1) HUE025195T2 (cg-RX-API-DMAC7.html)
IL (1) IL225763A (cg-RX-API-DMAC7.html)
MX (1) MX2013004427A (cg-RX-API-DMAC7.html)
TW (2) TWI511949B (cg-RX-API-DMAC7.html)
WO (1) WO2012052939A2 (cg-RX-API-DMAC7.html)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103153947B (zh) 2010-10-20 2015-11-25 埃科特莱茵药品有限公司 非对映选择性制备双环[2.2.2]辛-2-酮化合物
EP2630111B1 (en) * 2010-10-20 2015-02-25 Actelion Pharmaceuticals Ltd. Preparation of bicyclo[2.2.2]octan-2-one compounds

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3046106A1 (de) 1980-12-06 1982-07-15 Studiengesellschaft Kohle mbH, 4330 Mülheim Optisch reine bicyclo(2.2.2)oct-5-en-2.one, verfahren zu ihrer herstellung und ihre verwendung
JP3439255B2 (ja) * 1994-03-31 2003-08-25 長瀬産業株式会社 不斉マイケル反応を触媒する金属錯体
NZ581388A (en) 2007-04-27 2011-05-27 Actelion Pharmaceuticals Ltd Bridged six-membered ring compounds
EP2271628A1 (en) 2008-04-25 2011-01-12 Actelion Pharmaceuticals Ltd. Benzimidazole derivatives as calcium channel blockers
CN103153947B (zh) 2010-10-20 2015-11-25 埃科特莱茵药品有限公司 非对映选择性制备双环[2.2.2]辛-2-酮化合物
EP2630111B1 (en) * 2010-10-20 2015-02-25 Actelion Pharmaceuticals Ltd. Preparation of bicyclo[2.2.2]octan-2-one compounds

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
Elusive 6-exo-Hydroxybicyclo[2.2.2]octan-2-ones from the Corresponding Acetates by Methanolysis in the Presence of CH3ONa/La(OTf)3;Stefano，et al.;《ORGANIC LETTERS》;20020713;第4卷(第16期);2783-2785 *
Johansson,et al..Metal-Catalyzed a-Arylation of Carbonyl and Related Molecules: Novel Trends in C-C Bond Formation by C-H Bond Functionalization.《Angewandt Chemie International Edition》.2010,第49卷676-707. *
Nikolay T. Tzvetkov,et al..Synthesis of optically active (1R,4S,6S)-6-hydroxybicyclo[2.2.2]octan-2-one.《Tetrahedron: Asymmetry》.2006,第17卷993–998. *
On the Diastereoselectivity of the Aqueous-Acid-Catalyzed Intramolecular Aldol Condensation of 3-Oxocyclohexaneacetaldehydes;Barbara De Santis et al.;《Helvetica Chimica Acta》;19981216;第81卷;2375-2387 *
Synthesis of Bridged Steroids.III. Cholestane Derivatives having a Bridge Bicyclo[2.2.2]octane Ring System of the Atisine Type;Wataru Nagata，et al.;《Chemical & Pharmaceutical Bulletin》;19681231;第16卷(第5期);885-896 *

Also Published As

Publication number Publication date
EP2630111B1 (en) 2015-02-25
JP2013544796A (ja) 2013-12-19
ES2536897T3 (es) 2015-05-29
US9296673B2 (en) 2016-03-29
WO2012052939A2 (en) 2012-04-26
CA2813131C (en) 2019-02-12
JP5909237B2 (ja) 2016-04-26
CA2813131A1 (en) 2012-04-26
DK2630111T3 (en) 2015-04-20
TW201217324A (en) 2012-05-01
IL225763A0 (en) 2013-06-27
TWI511949B (zh) 2015-12-11
CN103168019A (zh) 2013-06-19
TWI551583B (zh) 2016-10-01
HUE025195T2 (en) 2016-02-29
EP2630111A2 (en) 2013-08-28
TW201217325A (en) 2012-05-01
IL225763A (en) 2016-04-21
KR20130138268A (ko) 2013-12-18
WO2012052939A3 (en) 2012-06-21
KR101876594B1 (ko) 2018-08-02
MX2013004427A (es) 2013-07-17
US20130211104A1 (en) 2013-08-15

Similar Documents

Publication Publication Date Title
Hernandez et al. Synthesis of (+)-and (-)-N-BOC-7-Azabicyclo [2.2. 1] heptan-2-ones, Versatile Intermediates for the Enantiospecific Synthesis of (+)-and (-)-Epibatidine and Analogs
CN103168019B (zh) 双环[2.2.2]辛-2-酮化合物的制备
CN103153947B (zh) 非对映选择性制备双环[2.2.2]辛-2-酮化合物
US20120130116A1 (en) Method for producing optically active 1-amino-2-vinylcyclopropanecarboxylic acid ester
JP2025527633A (ja) Ｇｌｙｔ－１阻害剤の調製のための拡張可能な方法
Yang et al. One-pot palladium-catalyzed racemization of (S)-praziquanamine: a key intermediate for the anthelmintic agent (R)-praziquantel
Paugam et al. Asymmetric synthesis of N-phenylethyl-2-phenyldecahydroquinolin-4-ones via Lewis acid catalyzed imino-Diels–Alder reaction
Pandey et al. Organocatalytic dynamic kinetic resolution via conjugate addition: synthesis of chiral trans-2, 5-dialkylcyclohexanones
Rahemtulla Development of cation-directed acylation reactions
Arai et al. ASYMMETRIC DIELS–ALDER REACTION OF 2-(p-TOLYLSULFI-NYL)-
Dupper Synthesis of Functionalized α, α-Dibromo Esters through Claisen Rearrangements of Dibromoketene Acetals and the Investigation of the Phosphine-Catalyzed [4+ 2] Annulation of Imines and Allenoates
Kaloko Synthesis of Novel Fused Tricyclic and Tetracyclic Skeletons Through Rhodium (I)-Catalyzed [2+ 2+ 2+ 1] Cycloaddition of Enediyne Derivatives with Carbon Monoxide
ITMI20120800A1 (it) Procedimento per la preparazione di un intermedio utile nella preparazione di un inibitore delle proteasi virali

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
TR01 Transfer of patent right

Effective date of registration: 20171103

Address after: Swiss A Skei Weil

Patentee after: ACTELION PHARMACEUTICALS LTD.

Address before: Swiss A Skei Weil

Patentee before: Actelion Pharmaceuticals Ltd.

TR01 Transfer of patent right
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20150527

CF01 Termination of patent right due to non-payment of annual fee