TW575537B - Process for the preparation of (R)-2-alkyl-3-phenyl-1-propanols - Google Patents
Process for the preparation of (R)-2-alkyl-3-phenyl-1-propanols Download PDFInfo
- Publication number
- TW575537B TW575537B TW90115928A TW90115928A TW575537B TW 575537 B TW575537 B TW 575537B TW 90115928 A TW90115928 A TW 90115928A TW 90115928 A TW90115928 A TW 90115928A TW 575537 B TW575537 B TW 575537B
- Authority
- TW
- Taiwan
- Prior art keywords
- alkyl
- formula
- patent application
- scope
- alkoxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 7
- -1 lithium ammonium amine Chemical class 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000010948 rhodium Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 description 3
- 229910052703 rhodium Inorganic materials 0.000 description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000006477 desulfuration reaction Methods 0.000 description 1
- 230000023556 desulfurization Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
Classifications
-
- 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
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
-
- 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
- C07C29/147—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 carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH13182000 | 2000-07-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW575537B true TW575537B (en) | 2004-02-11 |
Family
ID=4565375
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW90115928A TW575537B (en) | 2000-07-03 | 2001-06-29 | Process for the preparation of (R)-2-alkyl-3-phenyl-1-propanols |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6881868B2 (https=) |
| EP (1) | EP1296912B1 (https=) |
| JP (1) | JP4841799B2 (https=) |
| CN (1) | CN1293026C (https=) |
| AR (1) | AR029558A1 (https=) |
| AT (1) | ATE316518T1 (https=) |
| AU (1) | AU2001273762A1 (https=) |
| BR (1) | BR0112128A (https=) |
| CA (1) | CA2414844C (https=) |
| DE (1) | DE60116874T2 (https=) |
| TW (1) | TW575537B (https=) |
| WO (1) | WO2002002487A1 (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE323787T1 (de) * | 2002-12-18 | 2006-05-15 | Cardinal Cg Co | Plasmaunterstützte filmabscheidung |
| DE102005052195A1 (de) | 2005-10-28 | 2007-05-03 | Reuter Chemischer Apparatebau Kg | Verfahren zur Herstellung von chiralen Octensäurederivaten |
| US20090088576A1 (en) * | 2006-01-30 | 2009-04-02 | Peter Herold | Process for the Stereoselective Preparation of Alcohols From Alpha, Beta-Insaturated Compounds |
| EP1921069A1 (de) * | 2006-11-08 | 2008-05-14 | Speedel Experimenta AG | Verfahren zur Herstellung von 2-Alkyl-3-heterocyclyl-prop-2-en-1-olen |
| TW200837046A (en) * | 2006-11-08 | 2008-09-16 | Speedel Experimenta Ag | Process for preparing organic compounds |
| EP1939182A1 (de) * | 2006-12-22 | 2008-07-02 | Speedel Experimenta AG | Verfahren zur Herstellung von (R oder S)-2-Alkyl-3-heterocyclyl-1-propanolen |
| EP1958666A1 (en) | 2007-02-13 | 2008-08-20 | Speedel Experimenta AG | Heterocyclic-substituted alkanamides as therapeutic compounds |
| WO2008113835A1 (en) * | 2007-03-21 | 2008-09-25 | Novartis Ag | Process for preparing (r or s)-5-{1-azido-3-[6-methoxy-5-(3-methoxy-propoxy)-pyridin-3-ylmethyl]-4-methyl-pentyl}-3-alkyl-dihydro-furan-2-one |
| EP2178816A1 (en) * | 2007-07-11 | 2010-04-28 | DSM Fine Chemicals Austria Nfg GmbH & Co KG | Alpha-substituted , -unsaturated e- or z-aldehydes, use thereof, and processes for their preparation , |
| US8088954B2 (en) | 2007-07-11 | 2012-01-03 | Dsm Ip Assets B.V. | Preparation of a saturated aldehyde |
| DE102007049039A1 (de) | 2007-10-11 | 2009-04-16 | Reuter Chemischer Apparatebau Kg | Verfahren zur Herstellung von 8-Hydrazino-8-Aryl-Octanoylderivaten und deren Verwendung |
| US8203005B2 (en) | 2009-10-29 | 2012-06-19 | Carbo Design Llc | Manufacturing process for enantiomerically pure 8-aryloctanoic acids as Aliskiren |
| TW201202178A (en) | 2010-06-04 | 2012-01-16 | Chemo Iberica Sa | Process for producing Aliskiren |
| US8703976B2 (en) | 2011-10-02 | 2014-04-22 | Milan Soukup | Manufacturing process for 8-aryloctanoic acids such as Aliskiren |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2709268A1 (de) * | 1977-03-03 | 1978-09-07 | Merck Patent Gmbh | Diphenylaetherderivate, verfahren zu ihrer herstellung und pharmazeutische zubereitungen enthaltend diese verbindungen |
| ZA838831B (en) * | 1982-12-31 | 1984-07-25 | Fujisawa Pharmaceutical Co | New nitro aliphatic compounds,process for preparation thereof and use thereof |
| JPH0694441B2 (ja) * | 1992-11-18 | 1994-11-24 | 和光純薬工業株式会社 | ＤＬ−スレオ−２−（３，４−ジ低級アルキルオキシ−α−ヒドロキシベンジル）イソ吉草酸アルキル及びその製造法 |
| MY119161A (en) * | 1994-04-18 | 2005-04-30 | Novartis Ag | Delta-amino-gamma-hydroxy-omega-aryl-alkanoic acid amides with enzyme especially renin inhibiting activities |
| DE19516968A1 (de) * | 1995-05-12 | 1996-11-14 | Basf Ag | Optisch aktive Phosphine, deren Herstellung, deren Metallkomplexe und Anwendung in der asymmetrischen Synthese |
| WO2002002500A1 (en) * | 2000-07-03 | 2002-01-10 | Speedel Pharma Ag | Preparation of (r)-2-alkyl-3-phenylpropionic acids |
-
2001
- 2001-06-26 EP EP01940046A patent/EP1296912B1/en not_active Expired - Lifetime
- 2001-06-26 JP JP2002507746A patent/JP4841799B2/ja not_active Expired - Fee Related
- 2001-06-26 BR BR0112128-6A patent/BR0112128A/pt not_active IP Right Cessation
- 2001-06-26 US US10/312,992 patent/US6881868B2/en not_active Expired - Fee Related
- 2001-06-26 AU AU2001273762A patent/AU2001273762A1/en not_active Abandoned
- 2001-06-26 CN CNB018122337A patent/CN1293026C/zh not_active Expired - Fee Related
- 2001-06-26 WO PCT/CH2001/000398 patent/WO2002002487A1/en not_active Ceased
- 2001-06-26 DE DE60116874T patent/DE60116874T2/de not_active Expired - Lifetime
- 2001-06-26 CA CA2414844A patent/CA2414844C/en not_active Expired - Fee Related
- 2001-06-26 AT AT01940046T patent/ATE316518T1/de active
- 2001-06-29 TW TW90115928A patent/TW575537B/zh not_active IP Right Cessation
- 2001-07-03 AR ARP010103176A patent/AR029558A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2414844A1 (en) | 2002-01-10 |
| CN1440374A (zh) | 2003-09-03 |
| US6881868B2 (en) | 2005-04-19 |
| CN1293026C (zh) | 2007-01-03 |
| EP1296912A1 (en) | 2003-04-02 |
| DE60116874T2 (de) | 2006-11-02 |
| DE60116874D1 (de) | 2006-04-13 |
| WO2002002487A1 (en) | 2002-01-10 |
| JP2004502656A (ja) | 2004-01-29 |
| US20040092766A1 (en) | 2004-05-13 |
| JP4841799B2 (ja) | 2011-12-21 |
| EP1296912B1 (en) | 2006-01-25 |
| BR0112128A (pt) | 2003-05-13 |
| ATE316518T1 (de) | 2006-02-15 |
| CA2414844C (en) | 2010-05-11 |
| AR029558A1 (es) | 2003-07-02 |
| AU2001273762A1 (en) | 2002-01-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |