DK2368871T3 - Fremgangsmåde til fremstilling af (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenol - Google Patents

Fremgangsmåde til fremstilling af (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenol Download PDF

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Publication number
DK2368871T3
DK2368871T3 DK11004087.0T DK11004087T DK2368871T3 DK 2368871 T3 DK2368871 T3 DK 2368871T3 DK 11004087 T DK11004087 T DK 11004087T DK 2368871 T3 DK2368871 T3 DK 2368871T3
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compound
formula
carbon
dimethylamino
acid
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DK11004087.0T
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wolfgang dr Hell
Oswald Dr Zimmer
Helmut Heinrich Dr Buschmann
Jörg Dr Holenz
Stefan Dr Gladow
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Gruenenthal Gmbh
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    • 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
    • B01J25/00—Catalysts of the Raney type
    • B01J25/02—Raney nickel
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B57/00—Separation of optically-active compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
    • C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
    • C07C211/28—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by unsaturated carbon chains
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
    • 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
    • C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
    • C07C215/54—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
    • C07C217/62—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/64—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms
    • C07C217/66—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain
    • C07C217/72—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
    • C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C225/04—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated
    • C07C225/08—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated and containing rings
    • C07C225/10—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated and containing rings with doubly-bound oxygen atoms bound to carbon atoms not being part of rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Claims (7)

1. Fremgangsmåde til fremstilling af (lR,2R)-3-(3-dimethylamino-l-ethyl-2-methyl-propyl)-phenol, der har formlen (IV)
eller et syreadditionssalt deraf, hvilken fremgangsmåde omfatter de følgende trin: trin (a): at fremstille en forbindelse ifølge formel (II)
eventuelt i form af et syreadditionssalt, ved at reagere en forbindelse ifølge den generelle formel (I)
med ethylmagnesiumbromid eller ethylmagnesiumchlorid i en organisk ether valgt fra gruppen bestående af diethylether, tetrahyd rof uran, 2-methyltetrahydrofuran, tert-butyl-methylether eller en hvilken som helst blanding deraf under Grignard-betingelser; trin (b): at fremstille en forbindelse ifølge den generelle formel (III)
eventuelt i form af et syreadditionssalt, hvorved trin (b) udføres ved (b') at underkaste forbindelsen ifølge den generelle formel (II) til dehydrering og (b") at hydrere den således tilvejebragte forbindelse ifølge den generelle formel (VII)
ved anvendelse af en katalysator i et inert reaktionsmedium under tilstedeværelse af hydrogen; trin (c): at afbeskytte forbindelsen ifølge formel (III) for at tilvejebringe (1 R,2R)-3-(3-dimethylamino-l-ethyl-2-methyl-propyl)-phenol ifølge formel (IV); og eventuelt et trin (d), navnlig at konvertere forbindelse ifølge formel (IV) til et syreadditionssalt, hvor i ovennævnte forbindelser ifølge generelle formel (I), (II) og (III), R står for methyl, benzyl eller tetrahydropyranyl.
2. Fremgangsmåde ifølge krav 1, hvor trin (b) omfatter de følgende trin (b') og (b"), navnlig trin (b'): at underkaste forbindelsen ifølge den generelle formel (II) til en syrekatalyseret dehydreringsreaktion for at give en forbindelse ifølge formel (VII)
trin (b") at underkaste forbindelsen ifølge formel (VII) til en hydreringsreaktion ved heterogen katalyse under tilstedeværelse af hydrogen, hvor katalysatoren er valgt blandt en gruppe bestående af Raney-nikkel, palladium, palladium på carbon, platin, platin på carbon, ruthenium på carbon og rhodium på carbon.
3. Fremgangsmåde ifølge et hvilket som helst af krav 1 eller 2, hvor reaktionen ifølge trin (a) udføres i tetrahydrofuran med ethylmagnesiumchlorid ved en koncentration af ethyl-magnesiumchloriden fra 0,5 M til 2 M.
4. Fremgangsmåde ifølge et hvilket som helst af krav 1 til 3, hvor i forbindelserne ifølge den generelle formele (I), (II) og (III) R står for methyl.
5. Fremgangsmåde ifølge krav 4, hvor i trin (c), reageres forbindelsen ifølge formel (III) med brombrintesyre eller methansulfonsyre og methionin eller diisobutylaluminiumhy-drid i et reaktionsmedium, valgt fra gruppen bestående af diethylether, tetrahydrofuran, toluen, 2-methyltetrahydrofuran, dioxane, tert-butylmethylether og blandinger deraf for at opnå (1 R,2R)-3-(3-dimethylamino-l-ethyl-2-methyl-propyl)-phenol ifølge formel (IV).
6. Fremgangsmåde ifølge et hvilket som helst af krav 1 til 5, hvor den heterogene katalysator i hydreringstrinnet er valgt fra gruppen bestående af Raney-nikkel, palladium, palladium på carbon (1 - 10 vægt%), platin, platin på carbon (1 - 10 vægt%), ruthenium på carbon (1-10 vægt%) og rhodium på carbon (1-10 vægt%).
7. Fremgangsmåde ifølge et hvilket som helst af krav 1 til 5, hvor den heterogene katalysator i hydreringstrinnet er palladium på carbon (1 - 10 vægt%).
DK11004087.0T 2006-07-24 2007-07-23 Fremgangsmåde til fremstilling af (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenol DK2368871T3 (da)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP06015338 2006-07-24
EP07786260.5A EP2046724B1 (en) 2006-07-24 2007-07-23 Process for the preparation of (1r,2r)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol

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DK2368871T3 true DK2368871T3 (da) 2017-06-12

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Application Number Title Priority Date Filing Date
DK11004087.0T DK2368871T3 (da) 2006-07-24 2007-07-23 Fremgangsmåde til fremstilling af (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenol
DK17161440.7T DK3210965T3 (da) 2006-07-24 2007-07-23 Fremgangsmåde til fremstilling af (1r,2r)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol
DK07786260.5T DK2046724T3 (da) 2006-07-24 2007-07-23 Fremgangsmåde til fremstilling af (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol

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DK07786260.5T DK2046724T3 (da) 2006-07-24 2007-07-23 Fremgangsmåde til fremstilling af (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol

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US (7) US8877974B2 (da)
EP (4) EP3210965B1 (da)
JP (1) JP5612308B2 (da)
KR (1) KR101423996B1 (da)
CN (1) CN101495445B (da)
AU (1) AU2007278464C1 (da)
BR (1) BRPI0714558B8 (da)
CA (1) CA2657104C (da)
CO (1) CO6160221A2 (da)
CY (3) CY1115651T1 (da)
DK (3) DK2368871T3 (da)
ES (4) ES2901953T3 (da)
HK (2) HK1130246A1 (da)
HR (3) HRP20211902T1 (da)
HU (2) HUE056642T2 (da)
IL (3) IL196049A (da)
LT (2) LT3210965T (da)
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NO (2) NO341939B1 (da)
NZ (1) NZ573911A (da)
PL (3) PL2046724T3 (da)
PT (3) PT3210965T (da)
RU (1) RU2466124C2 (da)
SI (3) SI2368871T1 (da)
TW (2) TWI496762B (da)
WO (1) WO2008012047A1 (da)
ZA (1) ZA200900136B (da)

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