ES2093848T3 - Procedimiento para la preparacion de enantiomeros de cetonas. - Google Patents
Procedimiento para la preparacion de enantiomeros de cetonas.Info
- Publication number
- ES2093848T3 ES2093848T3 ES92920008T ES92920008T ES2093848T3 ES 2093848 T3 ES2093848 T3 ES 2093848T3 ES 92920008 T ES92920008 T ES 92920008T ES 92920008 T ES92920008 T ES 92920008T ES 2093848 T3 ES2093848 T3 ES 2093848T3
- Authority
- ES
- Spain
- Prior art keywords
- cir
- dichlorophenyl
- isopropyl
- butyl
- acid ester
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title abstract 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical compound C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 title 1
- 150000002576 ketones Chemical class 0.000 title 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- -1 ketobutanoic acid ester Chemical class 0.000 abstract 2
- JGMBHJNMQVKDMW-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C1C2=CC=CC=C2C(=O)CC1 JGMBHJNMQVKDMW-UHFFFAOYSA-N 0.000 abstract 1
- DPCXOOJTAKKWIC-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=C(Cl)C(Cl)=C1 DPCXOOJTAKKWIC-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical compound [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 abstract 1
- 238000006073 displacement reaction Methods 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000011968 lewis acid catalyst Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 229950009215 phenylbutanoic acid Drugs 0.000 abstract 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 abstract 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 229960002073 sertraline Drugs 0.000 abstract 1
- VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 abstract 1
- 230000000707 stereoselective effect Effects 0.000 abstract 1
Classifications
-
- 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
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D307/58—One oxygen atom, e.g. butenolide
-
- 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
- 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
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
- C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
-
- 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
- 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
- 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
- C07C67/31—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 functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
SE DESCRIBE UN NUEVO PROCESO MULTIETAPA PARA PREPARAR EL ENANTIOMERO OCESO IMPLICA (1) PRIMERO ESTERIFICACION DE ACIDO CETOBUTANOICO TER DEL ACIDO CETOBUTANOICO OBTENIDO EN LA PRIMERA ETAPA CON UN AGENTE DE REDUCCION CARBONILO ASIMETRICO PARA FORMAR EL CORRESPONDIENTE ISOPROPIL QUIRAL O TER-BUTIL 4 IL) DE ACIDO DIHIDROXIBUTANOICO SULFONIL O CLORURO O BROMURO DE TOLUENOSULFONIL IA DE UNA BASE ESTANDAR, PARA CONSEGUIR EL CORRESPONDIENTE ISOPROPIL O TER-BUTIL 4 OXIBUTANOATO; (4) DESPUES SOMETER EL ESTER DE ACIDO SULFONILOXIBUTANOICO ACOPLAMIENTO DE COBRE CON UN CUPRATO DE DILITIO DIFENIL (CIANO) DE LA FORMULA TETA2CU(CN)LI2 PARA EFECTUAR UN DESPLAZAMIENTO ESTEREOQUIMICO DEL GRUPO SULFONILOXI TIVO DIFENILCUPRATO DILITIO Y ASI FORMAR SELECTIVAMENTE EL CORRESPONDIENTE ISOPROPIL O TER-BUTIL 4 (4R) FENILBUTANOATO, Y (5) DESPUES CICLAR EL ESTER DE ACIDO N IZADOR ACIDO LEWIS, PARA FINALMENTE CONSEGUIR EL COMPUESTO NAFTALENONA LIDAD COMO INTERMEDIARIO QUE FINALMENTE CONDUCE AL NAFTALENAMINA AGENTE ANTIDEPRESIVO. EL ANTERIORMENTE MENCIONADO ISOPROPIL Y ESTERES DE TER-BUTIL DE ACIDO HIDROXIBUTANOICO ENCENOSULFONIL P ENTE MENCIONADO ISOPROPIL Y LOS ESTERES DE TER-BUTIL DE ACIDO FENILBUTANOICO ACIDOS ANTERIORMENTE DICHOS "PER SE". ESTOS NUEVOS COMPUESTOS QUIRAL SON TODOS UTILES COMO CLAVES INTERMEDIAS EN EL PROCESO GLOBAL DEL PRESENTE INVENTO.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80651991A | 1991-12-13 | 1991-12-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2093848T3 true ES2093848T3 (es) | 1997-01-01 |
Family
ID=25194226
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES92920008T Expired - Lifetime ES2093848T3 (es) | 1991-12-13 | 1992-09-15 | Procedimiento para la preparacion de enantiomeros de cetonas. |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP0624152B1 (es) |
| JP (1) | JP2709528B2 (es) |
| KR (2) | KR940703801A (es) |
| AT (1) | ATE145198T1 (es) |
| AU (1) | AU666867B2 (es) |
| CA (1) | CA2124454C (es) |
| DE (1) | DE69215235T2 (es) |
| DK (1) | DK0624152T3 (es) |
| ES (1) | ES2093848T3 (es) |
| FI (1) | FI106795B (es) |
| GR (1) | GR3022028T3 (es) |
| HU (1) | HU219398B (es) |
| IL (1) | IL104009A (es) |
| MX (1) | MX9207178A (es) |
| NO (1) | NO300729B1 (es) |
| NZ (2) | NZ245436A (es) |
| PT (1) | PT101119A (es) |
| TW (1) | TW226365B (es) |
| WO (1) | WO1993012062A1 (es) |
| ZA (1) | ZA929615B (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999046233A1 (fr) * | 1998-03-09 | 1999-09-16 | Sumika Fine Chemicals Co., Ltd. | Derives de l'alcool benzylique |
| PT1200387E (pt) | 1999-07-29 | 2004-09-30 | Ciba Sc Holding Ag | Processo para a hidrogenacao catalitica cis-selectiva de ciclo-hexilidenaminas |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4777288A (en) * | 1987-06-11 | 1988-10-11 | Pfizer Inc. | Process for preparing a 4,4-diphenylbutanoic acid derivative |
| US4839104A (en) * | 1987-06-11 | 1989-06-13 | Pfizer, Inc. | Process for preparing sertraline intermediates |
| US4921999A (en) * | 1988-08-23 | 1990-05-01 | General Electric Company | Method for making tertiary butyl esters |
-
1992
- 1992-09-15 AT AT92920008T patent/ATE145198T1/de not_active IP Right Cessation
- 1992-09-15 AU AU25832/92A patent/AU666867B2/en not_active Ceased
- 1992-09-15 DK DK92920008.7T patent/DK0624152T3/da active
- 1992-09-15 KR KR1019940702007A patent/KR940703801A/ko not_active IP Right Cessation
- 1992-09-15 HU HU9401763A patent/HU219398B/hu not_active IP Right Cessation
- 1992-09-15 EP EP92920008A patent/EP0624152B1/en not_active Expired - Lifetime
- 1992-09-15 CA CA002124454A patent/CA2124454C/en not_active Expired - Fee Related
- 1992-09-15 ES ES92920008T patent/ES2093848T3/es not_active Expired - Lifetime
- 1992-09-15 DE DE69215235T patent/DE69215235T2/de not_active Expired - Fee Related
- 1992-09-15 JP JP5510870A patent/JP2709528B2/ja not_active Expired - Fee Related
- 1992-09-15 WO PCT/US1992/007654 patent/WO1993012062A1/en active IP Right Grant
- 1992-09-23 TW TW081107522A patent/TW226365B/zh active
- 1992-12-07 IL IL104009A patent/IL104009A/en not_active IP Right Cessation
- 1992-12-11 NZ NZ245436A patent/NZ245436A/en unknown
- 1992-12-11 PT PT101119A patent/PT101119A/pt not_active Application Discontinuation
- 1992-12-11 ZA ZA929615A patent/ZA929615B/xx unknown
- 1992-12-11 MX MX9207178A patent/MX9207178A/es unknown
- 1992-12-11 NZ NZ270859A patent/NZ270859A/en unknown
-
1994
- 1994-06-10 FI FI942767A patent/FI106795B/fi active
- 1994-06-10 NO NO942184A patent/NO300729B1/no unknown
- 1994-06-11 KR KR94702007A patent/KR0136961B1/ko active
-
1996
- 1996-12-13 GR GR960403449T patent/GR3022028T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MX9207178A (es) | 1993-07-01 |
| KR0136961B1 (en) | 1998-04-25 |
| HU9401763D0 (en) | 1994-09-28 |
| FI942767A0 (fi) | 1994-06-10 |
| HUT67623A (en) | 1995-04-28 |
| DK0624152T3 (da) | 1996-12-30 |
| NZ245436A (en) | 1996-01-26 |
| TW226365B (es) | 1994-07-11 |
| IL104009A (en) | 1998-02-22 |
| DE69215235D1 (de) | 1996-12-19 |
| EP0624152B1 (en) | 1996-11-13 |
| JPH07502504A (ja) | 1995-03-16 |
| IL104009A0 (en) | 1993-05-13 |
| NO300729B1 (no) | 1997-07-14 |
| WO1993012062A1 (en) | 1993-06-24 |
| GR3022028T3 (en) | 1997-03-31 |
| FI106795B (fi) | 2001-04-12 |
| AU2583292A (en) | 1993-07-19 |
| NO942184L (es) | 1994-06-10 |
| ZA929615B (en) | 1994-06-13 |
| KR940703801A (ko) | 1994-12-12 |
| PT101119A (pt) | 1994-02-28 |
| DE69215235T2 (de) | 1997-03-06 |
| AU666867B2 (en) | 1996-02-29 |
| EP0624152A1 (en) | 1994-11-17 |
| CA2124454A1 (en) | 1993-06-24 |
| NO942184D0 (no) | 1994-06-10 |
| ATE145198T1 (de) | 1996-11-15 |
| CA2124454C (en) | 1997-08-26 |
| FI942767A (fi) | 1994-06-10 |
| NZ270859A (en) | 1996-01-26 |
| JP2709528B2 (ja) | 1998-02-04 |
| HU219398B (hu) | 2001-04-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Biloski et al. | A new. beta.-lactam synthesis | |
| Shono et al. | Electroorganic chemistry. 46. A new carbon-carbon bond forming reaction at the. alpha.-position of amines utilizing anodic oxidation as a key step | |
| Potin et al. | New chiral auxiliaries: their use in the asymmetric hydrogenation of. beta.-acetamidocrotonates | |
| US5399722A (en) | Process for preparing tert-butyl (3R,5S)-6-hydroxy-3,5--O--isopropylidene-3,5-dihydroxyhexanoate | |
| KR20000064735A (ko) | R-α-프로필-피페로닐 아민 및 그의 유사체의 신규 비대칭 합성 방법 | |
| US5196607A (en) | Process for preparing ketone enantiomer | |
| ES2093848T3 (es) | Procedimiento para la preparacion de enantiomeros de cetonas. | |
| DE3862434D1 (de) | Verfahren zur herstellung eines 4,4-diphenylbutansaeurederivats. | |
| JPH0625068A (ja) | 置換されたインダノン類の製造方法およびその用途 | |
| JPH069483A (ja) | 置換されたインダノン類の製造方法 | |
| Henegar et al. | A new method for the synthesis of dioxolenones via the carboxylation of ketone enolates with anisyl cyanoformate | |
| Johnson et al. | Microbial oxygenation of dialkylbenzenes (I) | |
| US5962706A (en) | Epoxides, process for their preparation and their use for the preparation of perfuming ingredients | |
| Yoshimatsu et al. | Z-selective or stereospecific alkenylation reaction: A novel synthetic method for α-fluoro-α, β-unsaturated esters | |
| Irie et al. | Lewis acid catalysed preparation of some carbamates and sulphonylureas. Application to the determination of enantiomeric purity of chiral alcohols | |
| Lauru et al. | Enantioselective synthesis of cyclopropylcarboxamides using s-BuLi–sparteine-mediated metallation | |
| EP0528694B1 (en) | Method for producing optically active 3-substituted-2-norbornanones and their intermediates | |
| KR100884558B1 (ko) | 고수율 및 고 광학순도의 광학활성 아미드의 제조방법 | |
| Argenti et al. | Asymmetric Synthesis of Highly Enantiomerically Enriched (S)(-)-β-Bisabolene | |
| Yasuhara et al. | Determination of the Absolute Configuration and Enantiomeric Purity of Allylic and Acetylenic Alcohols. | |
| US6111125A (en) | Preparation of (1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl methyl ketone and derivatives and stereoisomers of this compound | |
| JP3651009B2 (ja) | β−スルホキシ−γ−シリルアルコール及びその製造法 | |
| Matsuyama et al. | REGIOSELECTIVE ALKYLATION AND THE RAMBERG–BÄCKLUND TYPE REACTION OF α-(p-TOLYLSULFONYL) THIANE S, S-DIOXIDE. A NEW ROUTE TO THE SYNTHESIS OF 3-ALKYL-3-CYCLOPENTENONES | |
| Theodore et al. | Synthesis of deuterated optically active verapamil and gallopamil, and of N‐13C‐methyl‐verapamil | |
| CA2367936A1 (en) | Methods for producing .alpha.-acyloxy carbonyl compounds from enol ester epoxides |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG2A | Definitive protection |
Ref document number: 624152 Country of ref document: ES |