TWI551583B - 雙環［２.２.２］辛－２－酮化合物之製備 - Google Patents

雙環［２.２.２］辛－２－酮化合物之製備 Download PDF

Info

Publication number
TWI551583B
TWI551583B TW100137955A TW100137955A TWI551583B TW I551583 B TWI551583 B TW I551583B TW 100137955 A TW100137955 A TW 100137955A TW 100137955 A TW100137955 A TW 100137955A TW I551583 B TWI551583 B TW I551583B
Authority
TW
Taiwan
Prior art keywords
compound
formula
group
phenyl
ester
Prior art date
Application number
TW100137955A
Other languages
English (en)
Chinese (zh)
Other versions
TW201217324A (en
Inventor
斯戴凡 阿貝雷
雅各斯 亞利希斯 弗奈
Original Assignee
艾克泰聯製藥有限公司
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 艾克泰聯製藥有限公司 filed Critical 艾克泰聯製藥有限公司
Publication of TW201217324A publication Critical patent/TW201217324A/zh
Application granted granted Critical
Publication of TWI551583B publication Critical patent/TWI551583B/zh

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)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
TW100137955A 2010-10-20 2011-10-19 雙環［２.２.２］辛－２－酮化合物之製備 TWI551583B (zh)

Applications Claiming Priority (1)

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

Publications (2)

Publication Number Publication Date
TW201217324A TW201217324A (en) 2012-05-01
TWI551583B true TWI551583B (zh) 2016-10-01

Family

ID=45757740

Family Applications (2)

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
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

Family Applications After (1)

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

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) TWI551583B (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
ES2536897T3 (es) * 2010-10-20 2015-05-29 Actelion Pharmaceuticals Ltd. Preparación de compuestos de biciclo[2,2,2]octan-2-ona
KR101836552B1 (ko) 2010-10-20 2018-03-08 아이도시아 파마수티컬즈 리미티드 바이시클로[2.2.2]옥탄-2-온 화합물의 부분입체선택적 제조

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
JP4595040B2 (ja) 2007-04-27 2010-12-08 アクテリオン ファーマシューティカルズ リミテッド 架橋６員環化合物
KR101364909B1 (ko) 2008-04-25 2014-02-21 액테리온 파마슈티칼 리미티드 칼슘 채널 차단제로서의 벤지미다졸 유도체
ES2536897T3 (es) * 2010-10-20 2015-05-29 Actelion Pharmaceuticals Ltd. Preparación de compuestos de biciclo[2,2,2]octan-2-ona
KR101836552B1 (ko) 2010-10-20 2018-03-08 아이도시아 파마수티컬즈 리미티드 바이시클로[2.2.2]옥탄-2-온 화합물의 부분입체선택적 제조

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
B De Santis et al."On the Diastereoselectivity of the Aqueous‐Acid‐Catalyzed Intramolecular Aldol Condensation of 3‐Oxocyclohexaneacetaldehydes",Helvetica Chimica Acta Volume 81, Issue 12, pages 2375–2387, December 16, 1998 *
CCC Johansson, et al,"Metal‐Catalyzed α‐Arylation of Carbonyl and Related Molecules: Novel Trends in C C Bond Formation by C H Bond Functionalization", Angewandte Chemie International Edition ,Volume 49, Issue 4, pages 676–707, January 18, 2010 *
NT Tzvetkov,et al,"Synthesis of optically active (1R, 4S, 6S)-6-hydroxybicyclo [2.2. 2] octan-2-one", Tetrahedron: Asymmetry,Volume 17, Issue 6, 20 March 2006, Pages 993–998 *
S Di Stefano, et al."Elusive 6-e xo-Hydroxybicyclo [2.2. 2] octan-2-ones from the Corresponding Acetates by Methanolysis in the Presence of CH3ONa/La (OTf) 3",Org. Lett., 2002, 4 (16), pp 2783–2785. *
W NAGATA,et al,"Synthesis of Bridged Steroids. III. Cholestane Derivatives having a Bridged Bicyclo [2. 2. 2] octane Ring System of the Atisine Type",Chemical and Pharmaceutical Bulletin,Vol. 16 (1968) No. 5 P 885-896 *

Also Published As

Publication number Publication date
US20130211104A1 (en) 2013-08-15
CA2813131C (en) 2019-02-12
JP5909237B2 (ja) 2016-04-26
HUE025195T2 (en) 2016-02-29
IL225763A0 (en) 2013-06-27
CN103168019B (zh) 2015-05-27
KR101876594B1 (ko) 2018-08-02
JP2013544796A (ja) 2013-12-19
MX2013004427A (es) 2013-07-17
KR20130138268A (ko) 2013-12-18
WO2012052939A2 (en) 2012-04-26
ES2536897T3 (es) 2015-05-29
US9296673B2 (en) 2016-03-29
DK2630111T3 (en) 2015-04-20
TW201217324A (en) 2012-05-01
CA2813131A1 (en) 2012-04-26
EP2630111B1 (en) 2015-02-25
IL225763A (en) 2016-04-21
CN103168019A (zh) 2013-06-19
TWI511949B (zh) 2015-12-11
TW201217325A (en) 2012-05-01
WO2012052939A3 (en) 2012-06-21
EP2630111A2 (en) 2013-08-28

Similar Documents

Publication Publication Date Title
Flann et al. Enantioselective total synthesis of streptazolin. The tandem use of iminium ion vinylsilane cyclizations and intramolecular acylations
Bartlett et al. Evaluation of the claisen rearrangement of 2-cyclohexenols for the stereoselective construction of a terpene synthon
JP5909237B2 (ja) ビシクロ［２．２．２］オクタン−２−オン化合物の製造
Kaneko et al. Synthetic studies of huperzine A and its fluorinated analogues. 2. Synthesis and acetylcholinesterase inhibitory activity of novel fluorinated huperzine A analogues
White et al. Stereoselective, biogenetically patterned synthesis of (.+-.)-aplysistatin
JP5909238B2 (ja) ビシクロ［２．２．２］オクタン−２−オン化合物のジアステレオ選択的な製造
NO320332B1 (no) Fremgangsmate ved fremstilling av 2-azadihydroksybicyklo [2.2.2]-heptanforbindelser samt L-tartarsyresalter av forbindelsene
Feutren et al. Palladium catalysed formal 6-endo-trig approaches to pumiliotoxin alkaloids: interception of the elusive cyclopropyl intermediate
Cabanal-Duvillard et al. A Formal Asymmetric Synthesis of (−)-Epibatidine Using a Highly Diastereoselective Hetero Diels–Alder Reaction
Takemoto et al. Diastereoselective total synthesis of (-)-solavetivone via a copper-catalyzed conjugate addition of Me3Al to a cyclohexa-2, 5-dienone intermediate
Tkachenko et al. Terpenoid-derived β-ketoesters: ring expansion of camphor with diazoacetate and a few transformations of homocamphor-3-carboxylate
Solladié-Cavallo et al. 2-Chloro and 2-fluoro ketones derived from the chiral-pool
Tatsugi et al. A Facile Synthesis of 1-Alkyl-7-azalsatins
Sugimura et al. Chiral and flexible 2, 4-pentanediol-tethered cyclopropanation of olefins with a carbenoid derived from a diazo ester to construct three stereogenic centers
Paugam et al. Asymmetric synthesis of N-phenylethyl-2-phenyldecahydroquinolin-4-ones via Lewis acid catalyzed imino-Diels–Alder reaction
CN119504695A (zh) 一种药物中间体氮杂螺[4.5]癸烷衍生物的制备方法
Arai et al. ASYMMETRIC DIELS–ALDER REACTION OF 2-(p-TOLYLSULFI-NYL)-
BAXENDALE et al. REBECCA M. MYERS, KIMBERLEY A. ROPER
ITMI20120800A1 (it) Procedimento per la preparazione di un intermedio utile nella preparazione di un inibitore delle proteasi virali

Legal Events

Date Code Title Description
MM4A Annulment or lapse of patent due to non-payment of fees