FI90657B - Förfarande för framställning av 4-(3,4-diklorfenyl)-4-fenylbutansyra och mellanprodukter - Google Patents
Förfarande för framställning av 4-(3,4-diklorfenyl)-4-fenylbutansyra och mellanprodukter Download PDFInfo
- Publication number
- FI90657B FI90657B FI882779A FI882779A FI90657B FI 90657 B FI90657 B FI 90657B FI 882779 A FI882779 A FI 882779A FI 882779 A FI882779 A FI 882779A FI 90657 B FI90657 B FI 90657B
- Authority
- FI
- Finland
- Prior art keywords
- dichlorophenyl
- acid
- dihydro
- furanone
- solvent
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/15—Saturated compounds containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- 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
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- 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
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
- Medicinal Preparation (AREA)
- Catalysts (AREA)
Claims (10)
1. Förfarande för framställlning av 4-(3,4-diklor-fenyl)-4-fenylbutansyra, kännetecknat därav, 5 att (a) 4-(3,4-diklorfenyl)-4-ketobutansyra underkas-tas selektiv inverkan av ett karbonylreduktionsmedel i ett polärt protiskt eller aprotiskt lösningsmedel vid en temperatur av ca 0 - 100 °C tills reduktlonsreaktlonen 10 för bildande av den önskade 4-(3,4-diklorfenyl)-4-hydrox- ibutansyramellanprodukten är väsentligen fullständig; (b) den 1 steg (a) bildade hydroxisyramellan-produkten omvandlas tili 5-(3,4-diklorfenyl)-dihydro-2(3H)-furanon; och 15 (c) därefter omsätts den i steg (b) bildade gamma- laktonföreningen med bensen 1 ett överskott av nämnda reagens soin lösningsmedel eller 1 ett reaktionsinert or-ganiskt lösningsmedel i närvaro av en katalyt av Friedel-Crafts-typ vid en temperatur av ca 0 - 100 eC tills alky- 20 leringen av bensenet med nämnda gammalaktonförenlng för bildande av den önskade 4-(3,4-diklorfenyl)-4-fenylbutan-syran är väsentligen fullständig.
2. Förfarande enligt patentkravet 1, kännetecknat därav, att karbonylreduktionsmedlet, som 25 används i steget (a), är en aikaiimetallborhydrid.
3. Förfarande enligt patentkravet 2, kännetecknat därav, att det polära protiska lösnings-medlet, som används i steget (a), är vatten och reduk-tionsreaktionen utförs vid en temperatur av ca 50 - 30 75 °C.
4. Förfarande enligt patentkravet 1, kännetecknat därav, att omvandlingen av den i steget (a) bildade 4-(3,4-diklorfenyl)-4-hydroxibutansyramellan-produkten i steget (b) tili 5-(3,4-diklorfenyl)-dihydro- .35 2(3H)-furanon utförs genom att först isolera hydroxisyran 20 90657 frän reaktionsblandningen och därefter upphetta nämnda syra i ett kolvätelösningsmedel vid en temperatur av ca 55 - 150 °C tills omvandlingen tili den önskade gammalak-tonföreningen är väsentligen fullständig.
5 5. Förfarande enligt patentkravet 1, känne- t e c k n a t därav, att omvandlingen av den i steget (a) bildade 4-(3,4-diklorfenyl)-4-hydroxibutansyramellan-produkten i steget (b) tili 5-(3,4-diklor-fenyl)-dihydro-2(3H)-furanon utförs genom att upphetta hydroxisyran in 10 situ i ett vattenhaltigt vid en temperatur av ca 20 - 100 °C tills omvandlingen tili den önskade gammalakton-föreningen är väsentligen fullständig.
6. Förfarande enligt patentkravet 1, känne-t e c k n a t därav, att katalyten av Friedel-Crafts- 15 typ, som används i steget (c), är aluminiumklorid och Friedel-Crafts-alkyleringen utförs vid en temperatur av ca 10 - 30 °C.
7. Förfarande enligt patentkravet 6, känne-t e c k n a t därav, att den som utgängsämne i steget 20 (c) använda gammalaktonföreningens molförhällande tili bensenreagenset och aluminiumkloridkatalyten är ca 1,0:1,0 - 1,0:20,0 respektive 1,0:0,5 - 1,0:10,0.
8. Förfarande enligt patentkravet 1, känne-t e c k n a t därav, att det reaktionsinerta lösnings- 25 medlet, som används i steget (c), är metylenklorid eller o-diklorbensen, eller steget (c) utförs genom att använda bensenöverskott som lösningsmedel.
9. 5-(3,4-diklorfenyl)-dihydro-2(3H)-furanon.
10. 4-(3,4-diklorfenyl)-4-hydoxibutansyra eller 30 ett alkalimetall- eller aminadditionssalt därav.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI930935A FI91391C (sv) | 1987-06-11 | 1993-03-03 | Förfarande för framställning av 4-(3,4-diklorfenyl)-3,4-dihydro-1(2H)-naftalenon |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6057787 | 1987-06-11 | ||
| US07/060,577 US4777288A (en) | 1987-06-11 | 1987-06-11 | Process for preparing a 4,4-diphenylbutanoic acid derivative |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI882779A0 FI882779A0 (sv) | 1988-06-10 |
| FI882779A FI882779A (sv) | 1988-12-12 |
| FI90657B true FI90657B (sv) | 1993-11-30 |
| FI90657C FI90657C (sv) | 1994-03-10 |
Family
ID=22030394
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI882779A FI90657C (sv) | 1987-06-11 | 1988-06-10 | Förfarande för framställning av 4-(3,4-diklorfenyl)-4-fenylbutansyra och mellanprodukter |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US4777288A (sv) |
| EP (1) | EP0295050B1 (sv) |
| JP (1) | JPH0627098B2 (sv) |
| KR (1) | KR910000780B1 (sv) |
| CN (2) | CN1025328C (sv) |
| AT (1) | ATE62657T1 (sv) |
| AU (1) | AU586953B2 (sv) |
| CA (1) | CA1285574C (sv) |
| CS (1) | CS272238B2 (sv) |
| DD (2) | DD287483A5 (sv) |
| DE (1) | DE3862434D1 (sv) |
| DK (1) | DK175280B1 (sv) |
| EG (1) | EG18404A (sv) |
| ES (1) | ES2022621B3 (sv) |
| FI (1) | FI90657C (sv) |
| GR (1) | GR3001908T3 (sv) |
| HU (2) | HU213617B (sv) |
| IE (1) | IE61072B1 (sv) |
| IL (1) | IL86629A0 (sv) |
| MX (1) | MX172786B (sv) |
| MY (2) | MY103570A (sv) |
| NO (1) | NO167731C (sv) |
| NZ (1) | NZ224984A (sv) |
| PH (1) | PH25099A (sv) |
| PL (2) | PL153028B1 (sv) |
| PT (1) | PT87691B (sv) |
| RU (2) | RU1799377C (sv) |
| YU (2) | YU47120B (sv) |
| ZA (1) | ZA884161B (sv) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU219398B (hu) * | 1991-12-13 | 2001-04-28 | Pfizer Inc. | Eljárás dihidro-naftalinon-származék enantiomerjének előállítására |
| US5196607A (en) * | 1992-02-14 | 1993-03-23 | Pfizer Inc. | Process for preparing ketone enantiomer |
| US5466880A (en) * | 1992-09-15 | 1995-11-14 | Pfizer Inc. | Process for preparing ketone enantiomer |
| ES2108484T3 (es) * | 1993-11-30 | 1997-12-16 | Pfizer | Procedimiento para la preparacion de una tetralona asimetrica. |
| US6410794B1 (en) | 1994-12-16 | 2002-06-25 | Uop Llc | Process for preparation of pharmaceutically desired chiral tetralone from tetralones |
| SK180499A3 (en) | 1997-07-01 | 2001-08-06 | Pfizer | Sertraline salts and sustained-release dosage forms of sertraline |
| WO1999046233A1 (fr) * | 1998-03-09 | 1999-09-16 | Sumika Fine Chemicals Co., Ltd. | Derives de l'alcool benzylique |
| IL132500A0 (en) | 1998-10-29 | 2001-03-19 | Pfizer Prod Inc | Stereoselective microbial reduction of a racemic tetralone |
| IN187170B (sv) | 2000-01-04 | 2002-02-23 | Sun Pharmaceutical Ind Ltd | |
| FR2817256B1 (fr) * | 2000-11-27 | 2005-07-15 | Univ Pasteur | Derives de l'acides 4-hydroxybutanoique et de son homologue superieur comme ligands des recepteurs du gamma- hydroxybutyrate (ghb), compositions pharmaceutiques les contenant et utilisations pharmaceutiques |
| CN100413856C (zh) * | 2006-09-06 | 2008-08-27 | 大连来克精化有限公司 | 一种威士忌内酯的制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3412146A (en) * | 1965-08-13 | 1968-11-19 | Geigy Chem Corp | Process for preparation of diphenyl alkanoic acids |
| DE2112715A1 (de) * | 1971-03-17 | 1972-10-05 | Thomae Gmbh Dr K | Neue 4-(4-Biphenylyl)-4-hydroxybuttersaeuren,ihre Salze,Ester und Lactone |
| US4556676A (en) * | 1979-11-01 | 1985-12-03 | Pfizer Inc. | Antidepressant derivatives of trans-4-phenyl-1,2,3,4-tetrahydro-1-naphthalenamine |
| US4536518A (en) * | 1979-11-01 | 1985-08-20 | Pfizer Inc. | Antidepressant derivatives of cis-4-phenyl-1,2,3,4-tetrahydro-1-naphthalenamine |
| FR2504127B1 (fr) * | 1981-04-17 | 1985-07-19 | Roussel Uclaf | Nouveaux derives d'acides phenyl aliphatique carboxyliques, procede pour leur preparation et leur application comme medicaments |
| FR2521857B1 (fr) * | 1982-02-23 | 1985-10-31 | Solvay | Compositions pharmaceutiques contenant de l'acide 3-hydroxybutanoique ou un sel derive de cet acide et sels derives de l'acide 3-hydroxybutanoique et d'une base organique azotee |
| US4543428A (en) * | 1983-03-11 | 1985-09-24 | Oregon Graduate Center For Study & Research | Production of a hexahydronaphthalenone compound |
| DE3615157A1 (de) * | 1986-05-05 | 1987-11-12 | Schwabe Willmar Gmbh & Co | 5-arylalkyl-4-alkoxy-2(5h)-furanone, zwischenprodukte und verfahren zu ihrer herstellung sowie ihre anwendung als therapeutische wirkstoffe |
| US4855500A (en) * | 1988-05-04 | 1989-08-08 | Pfizer Inc. | Process for preparing a ketimine |
-
1987
- 1987-06-11 US US07/060,577 patent/US4777288A/en not_active Expired - Lifetime
-
1988
- 1988-06-06 IL IL86629A patent/IL86629A0/xx not_active IP Right Cessation
- 1988-06-06 MY MYPI88000602A patent/MY103570A/en unknown
- 1988-06-07 DE DE8888305179T patent/DE3862434D1/de not_active Expired - Fee Related
- 1988-06-07 AT AT88305179T patent/ATE62657T1/de not_active IP Right Cessation
- 1988-06-07 EP EP88305179A patent/EP0295050B1/en not_active Expired - Lifetime
- 1988-06-07 ES ES88305179T patent/ES2022621B3/es not_active Expired - Lifetime
- 1988-06-08 CS CS883976A patent/CS272238B2/cs not_active IP Right Cessation
- 1988-06-08 JP JP63141429A patent/JPH0627098B2/ja not_active Expired - Fee Related
- 1988-06-09 EG EG324/88A patent/EG18404A/xx active
- 1988-06-09 PT PT87691A patent/PT87691B/pt not_active IP Right Cessation
- 1988-06-09 CA CA000569010A patent/CA1285574C/en not_active Expired - Lifetime
- 1988-06-09 PL PL1988272949A patent/PL153028B1/pl unknown
- 1988-06-09 PL PL1988278118A patent/PL156829B1/pl unknown
- 1988-06-10 YU YU112788A patent/YU47120B/sh unknown
- 1988-06-10 KR KR1019880006962A patent/KR910000780B1/ko not_active IP Right Cessation
- 1988-06-10 MX MX011861A patent/MX172786B/es unknown
- 1988-06-10 NO NO882566A patent/NO167731C/no not_active IP Right Cessation
- 1988-06-10 DK DK198803190A patent/DK175280B1/da not_active IP Right Cessation
- 1988-06-10 PH PH37054A patent/PH25099A/en unknown
- 1988-06-10 AU AU17613/88A patent/AU586953B2/en not_active Ceased
- 1988-06-10 FI FI882779A patent/FI90657C/sv active IP Right Grant
- 1988-06-10 HU HU883018A patent/HU213617B/hu not_active IP Right Cessation
- 1988-06-10 DD DD88316663A patent/DD287483A5/de not_active IP Right Cessation
- 1988-06-10 HU HU883022A patent/HU198670B/hu not_active IP Right Cessation
- 1988-06-10 ZA ZA884161A patent/ZA884161B/xx unknown
- 1988-06-10 CN CN88103840A patent/CN1025328C/zh not_active Expired - Fee Related
- 1988-06-10 IE IE176288A patent/IE61072B1/en not_active IP Right Cessation
- 1988-06-10 RU SU884355975A patent/RU1799377C/ru active
- 1988-06-10 DD DD88325879A patent/DD279013A5/de not_active IP Right Cessation
- 1988-06-10 NZ NZ224984A patent/NZ224984A/en unknown
-
1989
- 1989-03-20 RU SU894613675A patent/RU1839670C/ru active
-
1991
- 1991-05-03 GR GR91400585T patent/GR3001908T3/el unknown
-
1992
- 1992-09-21 MY MYPI92001685A patent/MY107026A/en unknown
-
1993
- 1993-09-22 YU YU60893A patent/YU49242B/sh unknown
- 1993-12-03 CN CN93120776A patent/CN1042129C/zh not_active Expired - Fee Related
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BB | Publication of examined application | ||
| FG | Patent granted |
Owner name: PFIZER INC. |