BRPI0606851A2 - processo para a preparação de 3-aminoálcoois 1-substituìdos enantiomericamente puros - Google Patents

processo para a preparação de 3-aminoálcoois 1-substituìdos enantiomericamente puros

Info

Publication number
BRPI0606851A2
BRPI0606851A2 BRPI0606851-0A BRPI0606851A BRPI0606851A2 BR PI0606851 A2 BRPI0606851 A2 BR PI0606851A2 BR PI0606851 A BRPI0606851 A BR PI0606851A BR PI0606851 A2 BRPI0606851 A2 BR PI0606851A2
Authority
BR
Brazil
Prior art keywords
aryl
alkyl
preparation
substituted
optionally
Prior art date
Application number
BRPI0606851-0A
Other languages
English (en)
Inventor
Walter Brieden
Martin Clausen
John Mcgarrity
Hanspeter Mettler
Dominique Michel
Original Assignee
Lonza Ag
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 Lonza Ag filed Critical Lonza Ag
Publication of BRPI0606851A2 publication Critical patent/BRPI0606851A2/pt

Links

Classifications

    • 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
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
    • C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
    • C07C215/08—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with only one hydroxy group and one amino group bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
    • C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
    • 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
    • C07C213/02—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 involving the formation of amino groups from compounds containing 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
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
    • C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
    • C07C215/30—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings containing hydroxy groups and carbon atoms of six-membered aromatic rings bound to the same carbon atom of the carbon skeleton
    • 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
    • C07C225/14—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 unsaturated
    • C07C225/16—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 unsaturated and containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/04—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing only one sulfo group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/29—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings
    • C07C309/30—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings of six-membered aromatic rings substituted by alkyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)

Abstract

PROCESSO PARA A PREPARAçãO DE 3-AMINOáLCOOIS 1-SUBSTITUìDOS ENANTIOMERICAMENTE PUROS. é provido um processo para a preparação de sulfonatos de <225>-aminoálcool N-monosubstituído da fórmula (Ia), (Ib), em que R^ 1^ e aril C~ 6-20~ ou heteroaril C~ 4-12~ , cada um sendo opcionalmente substituído com um ou mais átomos de halogênio e/ou um ou mais grupos alquil C~ 1-4~, ou alcoxi C~ 1-4~, R^ 2^ e alquil C~ 1-4~, ou aril C~ 6-20~, cada aril sendo opcionalmente substituído com um ou mais átomos de halogênio e/ou um ou mais grupos alquil C~ 1-4~ ou alcoxi C~ 1-4~, e em queR^ 3^ é selecionado do grupo consistindo em resíduos de alquil C~ 1-18~, cicloalquil C~ 6-20~ , aril C~ 6-20~ e aralquil C~ 7-20~, compreendendo as etapas de a) reagir um metil cetona, uma amina primária, formaldeido e ácido sulfónico, em uma pressão acima de 1,5 bar, opcionalmente em um solvente orgânico, o solvente orgânico contendo opcionalmente água, para proporcionar sulfonatos de <225>-aminocetona N-substituída da fórmula (II), em que R^ 1^, R^ 2^ e R^ 3^ são como definidos acima, e b) hidrogenar assimetricamente os sulfonatos na presença de uma base e um catalisador, compreendendo um metal de transição e um ligante de difosfina, em um solvente polar, opcionalmente na presença de água.
BRPI0606851-0A 2005-02-21 2006-02-14 processo para a preparação de 3-aminoálcoois 1-substituìdos enantiomericamente puros BRPI0606851A2 (pt)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP05003657 2005-02-21
PCT/EP2006/001334 WO2006087166A1 (en) 2005-02-21 2006-02-14 Process for the preparation of enantiomerically pure 1-substituted-3-aminoalcohols

Publications (1)

Publication Number Publication Date
BRPI0606851A2 true BRPI0606851A2 (pt) 2009-07-21

Family

ID=34933850

Family Applications (1)

Application Number Title Priority Date Filing Date
BRPI0606851-0A BRPI0606851A2 (pt) 2005-02-21 2006-02-14 processo para a preparação de 3-aminoálcoois 1-substituìdos enantiomericamente puros

Country Status (12)

Country Link
US (2) US8258338B2 (pt)
EP (1) EP1868983A1 (pt)
JP (1) JP2008530161A (pt)
KR (1) KR20070104942A (pt)
CN (1) CN101124196B (pt)
AU (1) AU2006215811A1 (pt)
BR (1) BRPI0606851A2 (pt)
CA (1) CA2596909A1 (pt)
EA (1) EA200701613A1 (pt)
IL (1) IL185076A (pt)
NO (1) NO20074098L (pt)
WO (1) WO2006087166A1 (pt)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5154129B2 (ja) 2007-03-30 2013-02-27 ユニ・チャーム株式会社 複合シート及び複合シートを用いた吸収性物品
PL2426116T3 (pl) 2010-08-30 2013-11-29 Saltigo Gmbh Sposób wytwarzania (S)-3-N-metyloamino-1-(2-tienylo)-1-propanolu
CN105503490B (zh) * 2014-09-26 2020-07-03 上海交通大学 手性γ-仲胺基醇的制备方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB993584A (pt) * 1962-01-24
US4948813A (en) * 1987-11-30 1990-08-14 E. I. Du Pont De Nemours And Company Benzylketone phospholipase A2 inhibitors
CA2042346A1 (en) * 1990-05-17 1991-11-18 Michael Alexander Staszak Chiral synthesis of 1-aryl-3-aminopropan-1-ols
JPH0570412A (ja) * 1991-09-13 1993-03-23 Fuji Yakuhin Kogyo Kk 光学活性なβ−アミノアルコールの製造方法
PT1539673E (pt) * 2002-07-09 2007-11-14 Lonza Ag Processo para preparação de beta-aminoálcoois nmonossubstituídos
WO2004005307A1 (en) * 2002-07-09 2004-01-15 Lonza Ag Process for the preparation of optically active 3-n-methylamino-1-(2-thienyl)-1-propanol
JP4483165B2 (ja) * 2002-10-01 2010-06-16 山川薬品工業株式会社 光学活性な３−（メチルアミノ）−１−（２−チエニル）プロパン−１−オールの製造方法および製造の中間体
EP1720852B1 (en) * 2004-02-19 2012-07-11 Lonza AG Process for the preparation of enantiomerically pure 1-substituted-3-aminoalcohols

Also Published As

Publication number Publication date
EA200701613A1 (ru) 2008-02-28
US20090156833A1 (en) 2009-06-18
NO20074098L (no) 2007-11-19
IL185076A0 (en) 2007-12-03
CA2596909A1 (en) 2006-08-24
JP2008530161A (ja) 2008-08-07
CN101124196B (zh) 2011-05-11
AU2006215811A1 (en) 2006-08-24
HK1115578A1 (en) 2008-12-05
US20120316350A1 (en) 2012-12-13
KR20070104942A (ko) 2007-10-29
US8258338B2 (en) 2012-09-04
IL185076A (en) 2012-04-30
US8501967B2 (en) 2013-08-06
EP1868983A1 (en) 2007-12-26
WO2006087166A1 (en) 2006-08-24
CN101124196A (zh) 2008-02-13

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Legal Events

Date Code Title Description
B06A Patent application procedure suspended [chapter 6.1 patent gazette]
B08F Application dismissed because of non-payment of annual fees [chapter 8.6 patent gazette]

Free format text: REFERENTE A 9A ANUIDADE.

B08K Patent lapsed as no evidence of payment of the annual fee has been furnished to inpi [chapter 8.11 patent gazette]

Free format text: REFERENTE AO DESPACHO 8.6 PUBLICADO NA RPI 2308 DE 31/03/2015.