AR043771A1 - Procedimiento para producir alcoholes y aminas enriquecidos enantiomericamente - Google Patents
Procedimiento para producir alcoholes y aminas enriquecidos enantiomericamenteInfo
- Publication number
- AR043771A1 AR043771A1 ARP040100980A ARP040100980A AR043771A1 AR 043771 A1 AR043771 A1 AR 043771A1 AR P040100980 A ARP040100980 A AR P040100980A AR P040100980 A ARP040100980 A AR P040100980A AR 043771 A1 AR043771 A1 AR 043771A1
- Authority
- AR
- Argentina
- Prior art keywords
- mixture
- enriticially
- formula
- substituted
- heteroaryl
- Prior art date
Links
- 150000001412 amines Chemical class 0.000 title abstract 3
- 150000001298 alcohols Chemical class 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 abstract 5
- 125000001072 heteroaryl group Chemical group 0.000 abstract 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 125000004404 heteroalkyl group Chemical group 0.000 abstract 3
- 239000012327 Ruthenium complex Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- -1 cycloheteroalkyl Chemical group 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- 239000003446 ligand Substances 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- 125000003107 substituted aryl group Chemical group 0.000 abstract 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 150000002466 imines Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 150000003333 secondary alcohols Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
- C07C43/1782—Unsaturated ethers containing hydroxy or O-metal groups containing six-membered aromatic rings
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/52—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of imines or imino-ethers
-
- 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
- C07C29/143—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 ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
- C07C43/1786—Unsaturated ethers containing hydroxy or O-metal groups containing halogen
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/60—Reduction reactions, e.g. hydrogenation
- B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
- B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
- B01J2231/643—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of R2C=O or R2C=NR (R= C, H)
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/821—Ruthenium
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/26—All rings being cycloaliphatic the ring system containing ten carbon atoms
- C07C2602/28—Hydrogenated naphthalenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
Abstract
Método para producir un catalizador de reducción, el cual comprende: a) calentar una mezcla de un ligando, un complejo de rutenio, un alcohol secundario y b) separar los componentes volátiles de la mezcla. Reivindicación 11: Un método para reducir las cetonas e iminas de la fórmula (1), en la que R1 y R2 se seleccionan independientemente entre alquilo, alquenilo, cicloalquilo, heteroalquilo, cicloheteroalquilo, arilo, heteroarilo, arilo sustituido y heteroarilo sustituido; X es O o N-R3, en la que R3 es alquilo, heteroalquilo, cicloalquilo, heteroalquilo, cicloheteroalquilo, arilo, heteroarilo, arilo sustituido y heteroarilo sustituido; R1 y R2 considerados juntos pueden formar un anillo carbocíclico o heterocíclico sustituido o no sustituido, de 3 a 12 miembros; para producir alcoholes o aminas de la fórmula (2), en la que R1 y R2 son como se han descrito para la fórmula (1), es -OH o -NHR3 donde R3 es como se ha definido para la fórmula (1), caracterizado porque comprende: a) agitar una mezcla de un ligando, un complejo de rutenio y una amina terciaría en un disolvente seguido por la adición de una mezcla 5:2 molar de ácido fórmico y trietilamina; y b) anadir la cetona o la amina a la mezcla.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45779103P | 2003-03-26 | 2003-03-26 | |
| US45803503P | 2003-03-27 | 2003-03-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR043771A1 true AR043771A1 (es) | 2005-08-10 |
Family
ID=33101298
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP040100980A AR043771A1 (es) | 2003-03-26 | 2004-03-24 | Procedimiento para producir alcoholes y aminas enriquecidos enantiomericamente |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7045646B2 (es) |
| JP (1) | JP2006521201A (es) |
| AR (1) | AR043771A1 (es) |
| BR (1) | BRPI0408680A (es) |
| CA (1) | CA2520030A1 (es) |
| MX (1) | MXPA05010316A (es) |
| TW (1) | TW200510283A (es) |
| WO (1) | WO2004085058A1 (es) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006521201A (ja) | 2003-03-26 | 2006-09-21 | ファルマシア・アンド・アップジョン・カンパニー・エルエルシー | 鏡像異性体富化したアルコール類およびアミン類を製造する方法 |
| GB0425320D0 (en) | 2004-11-17 | 2004-12-22 | Johnson Matthey Plc | Diamines |
| ES2468415T3 (es) * | 2007-05-04 | 2014-06-16 | Mallinckrodt Llc | Procedimientos mejorados de preparación de opiáceos 6-alfa-hidroxi-N-alquilados |
| NZ582668A (en) * | 2007-07-17 | 2012-02-24 | Mallinckrodt Llc | Preparation of n-alkylated opiates by reductive amination |
| CN102227434B (zh) | 2008-09-30 | 2015-02-18 | 马林克罗特有限公司 | 选择性胺化酮吗啡喃的方法 |
| US8946419B2 (en) | 2009-02-23 | 2015-02-03 | Mallinckrodt Llc | (+)-6-hydroxy-morphinan or (+)-6-amino-morphinan derivatives |
| CN102459274B (zh) | 2009-06-11 | 2015-07-15 | 马林克罗特有限公司 | 6-酮基去甲吗啡喃通过催化氢转移的还原胺化 |
| US8519133B2 (en) | 2009-06-11 | 2013-08-27 | Mallinckrodt Llc | Preparation of 6-alpha-amino N-substituted morphinans by catalytic hydrogen transfer |
| CN103717601A (zh) | 2011-06-09 | 2014-04-09 | 马林克罗特有限公司 | 通过催化氢转移对6-酮基吗啡喃的还原胺化 |
| JO3192B1 (ar) | 2011-09-06 | 2018-03-08 | Novartis Ag | مركب بنزوثيازولون |
| PL2753622T3 (pl) | 2011-09-08 | 2016-07-29 | SpecGx LLC | Wytwarzanie alkaloidów bez oddzielania związków pośrednich |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0218675D0 (en) * | 2002-08-12 | 2002-09-18 | Ici Plc | Nitrogen-containing ligands |
| JP2006521201A (ja) | 2003-03-26 | 2006-09-21 | ファルマシア・アンド・アップジョン・カンパニー・エルエルシー | 鏡像異性体富化したアルコール類およびアミン類を製造する方法 |
-
2004
- 2004-03-15 JP JP2006506386A patent/JP2006521201A/ja active Pending
- 2004-03-15 BR BRPI0408680-5A patent/BRPI0408680A/pt not_active Application Discontinuation
- 2004-03-15 CA CA002520030A patent/CA2520030A1/en not_active Abandoned
- 2004-03-15 WO PCT/IB2004/000900 patent/WO2004085058A1/en not_active Ceased
- 2004-03-15 MX MXPA05010316A patent/MXPA05010316A/es not_active Application Discontinuation
- 2004-03-19 US US10/804,295 patent/US7045646B2/en not_active Expired - Fee Related
- 2004-03-23 TW TW093107781A patent/TW200510283A/zh unknown
- 2004-03-24 AR ARP040100980A patent/AR043771A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TW200510283A (en) | 2005-03-16 |
| US7045646B2 (en) | 2006-05-16 |
| CA2520030A1 (en) | 2004-10-07 |
| US20040230081A1 (en) | 2004-11-18 |
| MXPA05010316A (es) | 2005-11-17 |
| JP2006521201A (ja) | 2006-09-21 |
| BRPI0408680A (pt) | 2006-03-28 |
| WO2004085058A1 (en) | 2004-10-07 |
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| Date | Code | Title | Description |
|---|---|---|---|
| FB | Suspension of granting procedure |