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 PDF

Info

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
Application number
TW90115928A
Other languages
English (en)
Inventor
Peter Herold
Stefan Stutz
Felix Spindler
Original Assignee
Speedel Pharma 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 Speedel Pharma Ag filed Critical Speedel Pharma Ag
Application granted granted Critical
Publication of TW575537B publication Critical patent/TW575537B/zh

Links

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)

Description

575537
六、申請專利範圍 〆 第90 1 1 5928號「（R)-2-烷基-3-苯基-1-丙醇 專利案 (9 3年8月修正） 六、申請專利範圍： 1. 一種式I化合物之製法，
其中1^及R2各自爲氫、CVG烷基、CV 、CVC6烷氧基、CVG烷氧基烷基或 基-^-匕烷氧基，1^3爲CVC6烷基，包括 (a)於低溫且在第二鋰醯胺存在下，將式II 式I I I化合物反應， R1^^CH0RXT r\2 (其中1^及r2如上定義） O^C〇〇R7 ί之製法」 (工）， • C 6 _院基 Ci-q烷氧 化合物與 (II) , (III) , (其中R 3如上定義） 以形成式I V化合物， 575537 申請專利範圍
OH
(IV), 甲基） (b)分離式IV結晶化合物，將羥基醯化，然後在低溫 ._____________ 且含有鹼金屬醇化物之醯化製程的反應混合物中 進行脫去作用，形成式V化合物，R^Y^V^VCC)0R7 (V),
(C )於低溫且在作爲還原劑之金屬氫化物存在下，還 原式V之碳酸酯以形成式V I之醇類，及 R3 (VI), (d)於-20至150°C之溫度及105至2X107巴（巴斯卡 )之壓力條件下，於氫及具催化性質之金屬錯合 物存在下（不對稱氫化反應觸媒，包含釕、铑及 銥族金屬），氫化式VI之醇類’對掌性二配位基 配位體被鍵結，以形成式I化合物。 2.如申請專利範圍第1項之製法，其中R!爲甲氧基- C「 匸4烷氧基或乙氧基- 烷氧基’且R2爲甲氧基或乙 575537 六、申請專利範圍 氧基。 3. 如申請專利範圍第2項之製法，其中h爲1 -甲氧基 丙-3-氧基，且R2爲甲氧基。 4. 如申請專利範圍第1項之製法，其中R3爲線型或分 枝CVQ烷基。 5. 如申請專利範圍第4項之製法，其中R3爲異丙基。 6. 如申請專利範圍第1項之製法，其中h爲1 -甲氧基-正-丙氧基，R2爲甲氧基且R3爲異丙基。 7. 如申請專利範圍第1項之製法，其中步驟d)在作爲氫 化作用催化劑之式VII或Vila金屬錯合物存在下進 行， [LMeYZ] (VII) [LMeY] + E~ ( Vila) 其中 Me爲铑； Y代表二個烯烴或一個二烯； Ζ 爲 C1、B r 或 I ; E一爲氧酸或錯合酸之陰離子；且 L爲來自二第三二膦之基的對掌性配位體，其膦 基鍵結至二膦主鏈之（：2-(：4鏈，而二膦形成具有铑 之五至七員環。 8. 如申請專利範圍第7項之製法，其中L如式V I I I， 575537 六、申請專利範圍
、、 (VIII) 其中 m及η各自爲0或1至4之整數，卩8及R9爲氫或爲 相同或不同之取代基，其選自Ci~C4烷基或烷氧 基；且
Xi及x2相互獨立爲第二膦基。 9. 如申請專利範圍第8項之製法，其中取代基鍵結於第 6位置或第6,6’位置。 10. 如申請專利範圍第8或9項之製法，其中R8及R9爲 甲基、乙基、甲氧基或乙氧基。 11·如申請專利範圍第8項之製法’其中Xi與X2基可相 同或不同，且符合式邛^11’其中1^1{)及1^1爲相同 或不同，且爲分枝之C3-C8燒基、C3-C8環院基，或未 經取代之苯基或以1至3個CrC4烷基、Ci_c4烷氧基 或-CF3取代之苯基。 12·如申請專利範圍第8項之製法，其中式V〗丨I中η爲〇 ，\與Χ2爲PR^Rh基，其中於每一實例中Rl。及Rii 爲環丁基、環戊基、環己基、苯基或以1至2個甲基 、甲氧基或-CF3取代之苯基。 13·〜種如式V I之化合物， 575537 六、申請專利範圍
其中1及r2各自爲氫、CVC6烷基、Ci-C6鹵烷基 、（^-(：6烷氧基、cvc6烷氧基-(vc6烷基或cvc6烷氧 基- 院氧基’且1爲C^-C^院基。 14. 如申請專利範圍第1 3項之化合物，其中h爲甲氧基-匕-匕烷氧基或乙氧基烷氧基，R2爲甲氧基或乙 氧基，且R3爲CVC4烷基。 15. 如申請專利範圍第1 3項之化合物，其中&爲1 -甲氧 基-正-丙氧基，1?2爲甲氧基，且R3爲異丙基。 16. —種如式I V之化合物，
(IV), 其中1及R2各自爲氫、（VC6烷基、CVC6_烷基、 Ci -C6烷氧基、-C6烷氧基-Ci - C6烷基或Ci - C6烷氧基 -匕-匕烷氧基，r3爲cvc6烷基，且1爲cvc12烷基 、c3-cs環烷基、苯基或苯甲基。 17.如申請專利範圍第1 6項之化合物，其中R i爲甲氧基-(^-(：4烷氧基或乙氧基- 烷氧基，R2爲甲氧基或乙 575537 t、申請專利範圍 氧基，r3爲（VC4烷基，且r7爲cv 18.如申請專利範圍第1 6項之化合物， 氧基-正··丙氧基，R2爲甲氧基，R3 爲甲基或乙基。 C4烷基。 其中L爲1-甲 爲異丙基，且R7
TW90115928A 2000-07-03 2001-06-29 Process for the preparation of (R)-2-alkyl-3-phenyl-1-propanols TW575537B (en)

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 (zh)
EP (1) EP1296912B1 (zh)
JP (1) JP4841799B2 (zh)
CN (1) CN1293026C (zh)
AR (1) AR029558A1 (zh)
AT (1) ATE316518T1 (zh)
AU (1) AU2001273762A1 (zh)
BR (1) BR0112128A (zh)
CA (1) CA2414844C (zh)
DE (1) DE60116874T2 (zh)
TW (1) TW575537B (zh)
WO (1) WO2002002487A1 (zh)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1579027B1 (en) * 2002-12-18 2006-04-19 Cardinal CG Company Plasma-enhanced film deposition
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
AR065792A1 (es) * 2007-03-21 2009-07-01 Speedel Experimenta Ag Proceso para preparar (r o s) -5- (1 -azido-3-(6-metoxi-5-(3-metoxi-propoxi) -piridin-3-ilmetil) -4-metil- pentil) -3-alquil-dihidro-furan-2-ona
WO2009007462A1 (en) * 2007-07-11 2009-01-15 Dsm Fine Chemicals Austria Nfg Gmbh & Co. Kg ALPHA-SUBSTITUTED α,β-UNSATURATED E- OR Z-ALDEHYDES, USE THEREOF, AND PROCESSES FOR THEIR PREPARATION α,β
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)

* Cited by examiner, † Cited by third party
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
EP1296927B1 (en) * 2000-07-03 2012-02-22 Novartis AG Preparation of (r)-2-alkyl-3-phenylpropionic acids

Also Published As

Publication number Publication date
JP2004502656A (ja) 2004-01-29
CA2414844C (en) 2010-05-11
US6881868B2 (en) 2005-04-19
AU2001273762A1 (en) 2002-01-14
BR0112128A (pt) 2003-05-13
EP1296912B1 (en) 2006-01-25
ATE316518T1 (de) 2006-02-15
CN1440374A (zh) 2003-09-03
CA2414844A1 (en) 2002-01-10
CN1293026C (zh) 2007-01-03
JP4841799B2 (ja) 2011-12-21
DE60116874D1 (de) 2006-04-13
EP1296912A1 (en) 2003-04-02
AR029558A1 (es) 2003-07-02
US20040092766A1 (en) 2004-05-13
WO2002002487A1 (en) 2002-01-10
DE60116874T2 (de) 2006-11-02

Similar Documents

Publication Publication Date Title
TW575537B (en) Process for the preparation of (R)-2-alkyl-3-phenyl-1-propanols
Abdur‐Rashid et al. Synthesis of ruthenium hydride complexes containing beta‐aminophosphine ligands derived from amino acids and their use in the H2‐hydrogenation of ketones and imines
ES2220826T3 (es) Nuevos compuestos de n-fenilpirrol-bisfosfano y sus complejos metalicos.
JP4244212B2 (ja) Ｃ、ｐキラルホスフィン二座配位子
JP6393322B2 (ja) 新規なキラル窒素−リン配位子及びアルケン類の不斉水素化のためのその使用
JP2004502663A5 (zh)
CA2192226C (en) Ruthenium complexes with a chiral, bidentate phosphine/oxazoline ligand for enantioselective transfer hydrogenation of prochiral ketones
CN111315753A (zh) 用于在金属配合物和均相催化中使用的内鎓盐官能化的磷烷
CN105585593A (zh) 新型含吡啶基冠醚的手性双磷配体及其在不对称催化反应中的应用
JP2004502656A5 (zh)
US20130244865A1 (en) Metal Complex Compound, Hydrogen Production Catalyst and Hydrogenation Reaction Catalyst Each Comprising the Metal Complex Compound, and Hydrogen Production Method and Hydrogenation Method Each Using the Catalyst
TW200813079A (en) Method for making optically active amino phosphinylbutanoic acids
JP4597466B2 (ja) ルテニウム化合物を製造する方法
CN114478362A (zh) 一种手性吡啶醇衍生物的制备方法
CA2348595A1 (en) Diphosphines
CA2591126A1 (en) Process for the preparation of aminiphosphine ligands and their use in metal catalysts
JP2002187895A5 (zh)
CN110156832A (zh) 双缩醛基苯基膦、它们的制备方法及在偶联反应中的用途
WO2003040149A2 (en) Asymmetric catalysis based on chiral phospholanes and hydroxyl phospholanes
WO2005016943A1 (ja) 新規な遷移金属錯体、及び該錯体を用いた光学活性アルコールの製造法
JP6213991B2 (ja) ロジウム触媒、およびこれを用いる光学活性化合物の製造方法
JP5507931B2 (ja) 芳香族複素環をもつ光学活性アルコールの製造方法
JP2003176293A (ja) キラル一リン化合物、該化合物を含有する触媒およびキラル化合物の製造方法
CN113234104B (zh) 钳形钼配合物及其制备方法、催化组合物和应用及醇制备方法
US6906213B1 (en) Preparation of aminophosphines

Legal Events

Date Code Title Description
MM4A Annulment or lapse of patent due to non-payment of fees