TWI511949B - 雙環［２．２．２］辛－２－酮化合物之非對映選擇性製備 - Google Patents

雙環［２．２．２］辛－２－酮化合物之非對映選擇性製備 Download PDF

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Publication number
TWI511949B
TWI511949B TW100137956A TW100137956A TWI511949B TW I511949 B TWI511949 B TW I511949B TW 100137956 A TW100137956 A TW 100137956A TW 100137956 A TW100137956 A TW 100137956A TW I511949 B TWI511949 B TW I511949B
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TW
Taiwan
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compound
formula
base
equivalents
cyclohexen
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TW100137956A
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English (en)
Chinese (zh)
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TW201217325A (en
Inventor
Stefan Abele
Jacques-Alexis Funel
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Actelion Pharmaceuticals Ltd
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Publication of TW201217325A publication Critical patent/TW201217325A/zh
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    • 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
    • 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
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
TW100137956A 2010-10-20 2011-10-19 雙環［２．２．２］辛－２－酮化合物之非對映選擇性製備 TWI511949B (zh)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IB2010054747 2010-10-20

Publications (2)

Publication Number Publication Date
TW201217325A TW201217325A (en) 2012-05-01
TWI511949B true TWI511949B (zh) 2015-12-11

Family

ID=45757740

Family Applications (2)

Application Number Title Priority Date Filing Date
TW100137956A TWI511949B (zh) 2010-10-20 2011-10-19 雙環［２．２．２］辛－２－酮化合物之非對映選擇性製備
TW100137955A TWI551583B (zh) 2010-10-20 2011-10-19 雙環［２.２.２］辛－２－酮化合物之製備

Family Applications After (1)

Application Number Title Priority Date Filing Date
TW100137955A TWI551583B (zh) 2010-10-20 2011-10-19 雙環［２.２.２］辛－２－酮化合物之製備

Country Status (13)

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

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012052939A2 (en) * 2010-10-20 2012-04-26 Actelion Pharmaceuticals Ltd Preparation of bicyclo[2.2.2]octan-2-one compounds
DK2630120T3 (en) 2010-10-20 2018-10-08 Idorsia Pharmaceuticals Ltd DIASTEREOSELECTIVE PREPARATION OF BICYCLO [2.2.2] OCTAN-2-ON COMPOUNDS

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008132679A1 (en) * 2007-04-27 2008-11-06 Actelion Pharmaceuticals Ltd Bridged six-membered ring compounds
TW201217324A (en) * 2010-10-20 2012-05-01 Actelion Pharmaceuticals Ltd Preparation of bicyclo[2.2.2]octan-2-one compounds

Family Cites Families (4)

* 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
AU2009239620A1 (en) 2008-04-25 2009-10-29 Actelion Pharmaceuticals Ltd Benzimidazole derivatives as calcium channel blockers
DK2630120T3 (en) 2010-10-20 2018-10-08 Idorsia Pharmaceuticals Ltd DIASTEREOSELECTIVE PREPARATION OF BICYCLO [2.2.2] OCTAN-2-ON COMPOUNDS

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008132679A1 (en) * 2007-04-27 2008-11-06 Actelion Pharmaceuticals Ltd Bridged six-membered ring compounds
TW201217324A (en) * 2010-10-20 2012-05-01 Actelion Pharmaceuticals Ltd Preparation of bicyclo[2.2.2]octan-2-one compounds

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Bella et al., "Synergic Asymmetric Organocatalysis (SAOc) of Cinchona Alkaloids and Secondary Amines in the Synthesis of Bicyclo [2.2.2] octan-2-ones", Chemical Communication, 2009, No.5, pages 597-599 *
Yang and Carter, "Organocatalyzed, Enantioselective Synthesis of Bicyclo-[2.2.2]-Octanes Containing Benzylic, All-Carbon Quaternary Centers", Tetrahedron, 2010, Vol.66, No.26, pages 4854-4859. *

Also Published As

Publication number Publication date
CN103168019A (zh) 2013-06-19
CA2813131C (en) 2019-02-12
KR101876594B1 (ko) 2018-08-02
DK2630111T3 (en) 2015-04-20
TW201217325A (en) 2012-05-01
TW201217324A (en) 2012-05-01
US20130211104A1 (en) 2013-08-15
EP2630111B1 (en) 2015-02-25
JP2013544796A (ja) 2013-12-19
CA2813131A1 (en) 2012-04-26
JP5909237B2 (ja) 2016-04-26
ES2536897T3 (es) 2015-05-29
CN103168019B (zh) 2015-05-27
EP2630111A2 (en) 2013-08-28
KR20130138268A (ko) 2013-12-18
US9296673B2 (en) 2016-03-29
IL225763A (en) 2016-04-21
TWI551583B (zh) 2016-10-01
MX2013004427A (es) 2013-07-17
WO2012052939A2 (en) 2012-04-26
WO2012052939A3 (en) 2012-06-21
IL225763A0 (en) 2013-06-27
HUE025195T2 (en) 2016-02-29

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