JP2007519655A - 鏡像異性的に純粋なアミノアルコールの調製方法 - Google Patents
鏡像異性的に純粋なアミノアルコールの調製方法 Download PDFInfo
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- JP2007519655A JP2007519655A JP2006550005A JP2006550005A JP2007519655A JP 2007519655 A JP2007519655 A JP 2007519655A JP 2006550005 A JP2006550005 A JP 2006550005A JP 2006550005 A JP2006550005 A JP 2006550005A JP 2007519655 A JP2007519655 A JP 2007519655A
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- enantiomerically pure
- lipase
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- 238000000034 method Methods 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims description 8
- 150000001414 amino alcohols Chemical class 0.000 title abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 23
- 102000004882 Lipase Human genes 0.000 claims abstract description 19
- 108090001060 Lipase Proteins 0.000 claims abstract description 19
- 239000004367 Lipase Substances 0.000 claims abstract description 19
- 235000019421 lipase Nutrition 0.000 claims abstract description 19
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000002148 esters Chemical class 0.000 claims abstract description 15
- 150000002576 ketones Chemical class 0.000 claims abstract description 7
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229940014800 succinic anhydride Drugs 0.000 claims abstract description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- 239000001384 succinic acid Substances 0.000 claims description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- 241000589516 Pseudomonas Species 0.000 claims description 4
- 241001453380 Burkholderia Species 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- ZEUITGRIYCTCEM-KRWDZBQOSA-N (S)-duloxetine Chemical compound C1([C@@H](OC=2C3=CC=CC=C3C=CC=2)CCNC)=CC=CS1 ZEUITGRIYCTCEM-KRWDZBQOSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 229960002866 duloxetine Drugs 0.000 description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
- MSLOAFIOTOHDIE-UHFFFAOYSA-N 3-chloro-1-thiophen-2-ylpropan-1-one Chemical compound ClCCC(=O)C1=CC=CS1 MSLOAFIOTOHDIE-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YEJVVFOJMOHFRL-ZETCQYMHSA-N (1s)-3-(methylamino)-1-thiophen-2-ylpropan-1-ol Chemical compound CNCC[C@H](O)C1=CC=CS1 YEJVVFOJMOHFRL-ZETCQYMHSA-N 0.000 description 1
- YISRPYKYTBBHBK-LURJTMIESA-N (1s)-3-chloro-1-thiophen-2-ylpropan-1-ol Chemical compound ClCC[C@H](O)C1=CC=CS1 YISRPYKYTBBHBK-LURJTMIESA-N 0.000 description 1
- NMLRFGBDXFMJJM-LMOVPXPDSA-N (3s)-n-methyl-3-naphthalen-1-yloxy-3-thiophen-2-ylpropan-1-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C1([C@@H](OC=2C3=CC=CC=C3C=CC=2)CCNC)=CC=CS1 NMLRFGBDXFMJJM-LMOVPXPDSA-N 0.000 description 1
- YISRPYKYTBBHBK-UHFFFAOYSA-N 3-chloro-1-thiophen-2-ylpropan-1-ol Chemical compound ClCCC(O)C1=CC=CS1 YISRPYKYTBBHBK-UHFFFAOYSA-N 0.000 description 1
- 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 class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 241000134107 Burkholderia plantarii Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 241000589540 Pseudomonas fluorescens Species 0.000 description 1
- 241000589538 Pseudomonas fragi Species 0.000 description 1
- 241000218905 Pseudomonas luteola Species 0.000 description 1
- 241000577556 Pseudomonas wisconsinensis Species 0.000 description 1
- 241000607626 Vibrio cholerae Species 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- -1 alkali metal salt Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036983 biotransformation Effects 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010353 genetic engineering Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000012460 protein solution Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940118696 vibrio cholerae Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
Abstract
Description
(i) 式3で表されるケトンを式4で表されるラセミ体のアルコールに還元する工程、
(ii) 式4で表されるラセミ体のアルコールをリパーゼの存在下に無水コハク酸で鏡像異性選択的にアシル化して式7で表されるコハク酸半エステルを得る工程、
(iii) 式7で表されるコハク酸半エステルを式4で表される未反応鏡像異性体から分離する工程、
(iv) 式4で表される鏡像異性的に純粋なアルコールをメチルアミンと反応させて式1で表される鏡像異性的に純粋なアルコールを得る工程、
を含む。
0℃において、204g(1.21モル)のケトン3を、トルエン400mLとメタノール200gからなる混合物に、初めに導入した。30%NaOHを2g加えたあと、ホウ水素化ナトリウム21.4gを2.5時間かけて少しずつ加えた。この反応混合物を0℃にて40分間撹拌したあと、これを氷冷の10%酢酸500mLに加えた。水相を分離したあと、有機相を硫酸ナトリウムで乾燥させその溶媒を取り除いた。5を約10%含有する198gの4を得た。
アルコール5を10%含有している197g(1.16モル)のアルコール4(すなわち実施例1で得られた反応生成物)を、1リットルのMTBEに、初めに導入した。無水コハク酸64.4g(0.64モル)およびBurkholderia plantariiリパーゼ10gを次に加えた。この混合物を室温にて20時間撹拌し、この酵素を濾過により除去した。水1.4Lを加えたあと、この混合物を炭酸ナトリウムでpH=9に調整し、水相を分離した。有機相を硫酸ナトリウムで乾燥させて溶媒を取り除いた。対応する対掌体5を約10%含有する96gの6を得た。
対応する対掌体5を約10%含有する20g(0.093モル)のアルコール6(すなわち実施例2の反応生成物)を、加圧器中で、メタノール40gに初めに導入し、そのあとメチルアミンの40%水溶液74gを加え、この混合物を、固有圧力下で、75℃にて20時間撹拌した。反応を終わりまで行った後、30%NaOHを5g加え、その混合物を80℃にて10分間撹拌した。溶媒を除去し、残留物をトルエン100mL中に取り込んだ。不溶解性の成分を濾過除去したあと、その残留物を、シクロヘキサンから再結晶させた。
無色の結晶1を13.17g得た(回転角度:MeOH中 c=1、α[D]25℃=-13.2°、光学的純粋生成物に対応している)。
Claims (10)
- 前記工程(i)における還元をNaBH4を用いて行う請求項1に記載の方法。
- 前記工程(ii)におけるリパーゼが固定化リパーゼである請求項1に記載の方法。
- 前記工程(ii)におけるリパーゼがBurkholderiaまたはPseudomonasから誘導されたものである請求項1に記載の方法。
- 前記工程(iii)における分離が式7で表されるコハク酸半エステルの共役塩基の形態で行われる請求項1に記載の方法。
- 前記工程(ii)の反応が溶媒として炭化水素中で行われる請求項1に記載の方法。
- 前記溶媒としてヘプタンが用いられる請求項6に記載の方法。
- 前記方法が連続的に操作される請求項1に記載の方法。
- 固定化リパーゼがカラム反応器中で用いられる請求項8に記載の方法。
- 工程(ii)における溶媒としてエチレンカーボネートまたはプロピレンカーボネートを用いる請求項9に記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102004004719A DE102004004719A1 (de) | 2004-01-29 | 2004-01-29 | Verfahren zur Herstellung von enantiomerenreinen Aminoalkoholen |
PCT/EP2005/000420 WO2005073215A1 (de) | 2004-01-29 | 2005-01-18 | Verfahren zur herstellung von enantiomerenreinen aminoalkoholen |
Publications (1)
Publication Number | Publication Date |
---|---|
JP2007519655A true JP2007519655A (ja) | 2007-07-19 |
Family
ID=34801277
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006550005A Pending JP2007519655A (ja) | 2004-01-29 | 2005-01-18 | 鏡像異性的に純粋なアミノアルコールの調製方法 |
Country Status (10)
Country | Link |
---|---|
US (1) | US7435835B2 (ja) |
EP (1) | EP1713788B1 (ja) |
JP (1) | JP2007519655A (ja) |
CN (1) | CN100491369C (ja) |
AT (1) | ATE424392T1 (ja) |
DE (2) | DE102004004719A1 (ja) |
DK (1) | DK1713788T3 (ja) |
ES (1) | ES2320354T3 (ja) |
PT (1) | PT1713788E (ja) |
WO (1) | WO2005073215A1 (ja) |
Cited By (1)
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WO2010123067A1 (ja) * | 2009-04-23 | 2010-10-28 | 株式会社カネカ | (s)-1-置換プロパン-1-オール誘導体の製造方法 |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
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CA2656128A1 (en) | 2006-07-03 | 2008-01-10 | Ranbaxy Laboratories Limited | Process for the preparation of enantiomerically pure salts of n-methyl-3(1-naphthaleneoxy)-3-(2-thienyl)propanamine |
CN101045936B (zh) * | 2007-03-27 | 2010-06-23 | 吉林大学 | 以酸酐为酰基供体制备手性脂肪醇的方法 |
SI2558455T1 (sl) | 2010-04-13 | 2017-12-29 | Krka, D.D., Novo Mesto | Sinteza duloksetina in/ali njegovih farmacevtsko sprejemljivih soli |
WO2012069974A1 (en) * | 2010-11-26 | 2012-05-31 | Basf Se | Preparation of isomerically pure substituted cyclohexanols |
US8709751B2 (en) | 2010-11-26 | 2014-04-29 | Basf Se | Preparation of isomerically pure substituted cyclohexanols |
US20130273619A1 (en) | 2012-04-16 | 2013-10-17 | Basf Se | Process for the Preparation of (3E, 7E)-Homofarnesol |
CN103614450A (zh) * | 2013-12-19 | 2014-03-05 | 黑龙江省科学院微生物研究所 | 脂肪酶催化拆分dl-薄荷醇的方法 |
FI126970B (en) | 2014-12-22 | 2017-08-31 | Picosun Oy | Atomic layer cultivation in which the first and second species of source materials are present simultaneously |
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2004
- 2004-01-29 DE DE102004004719A patent/DE102004004719A1/de not_active Withdrawn
-
2005
- 2005-01-18 ES ES05700995T patent/ES2320354T3/es active Active
- 2005-01-18 US US10/587,440 patent/US7435835B2/en not_active Expired - Fee Related
- 2005-01-18 CN CNB2005800036708A patent/CN100491369C/zh not_active Expired - Fee Related
- 2005-01-18 DK DK05700995T patent/DK1713788T3/da active
- 2005-01-18 PT PT05700995T patent/PT1713788E/pt unknown
- 2005-01-18 DE DE502005006744T patent/DE502005006744D1/de active Active
- 2005-01-18 EP EP05700995A patent/EP1713788B1/de not_active Not-in-force
- 2005-01-18 AT AT05700995T patent/ATE424392T1/de not_active IP Right Cessation
- 2005-01-18 JP JP2006550005A patent/JP2007519655A/ja active Pending
- 2005-01-18 WO PCT/EP2005/000420 patent/WO2005073215A1/de not_active Application Discontinuation
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JPH02142495A (ja) * | 1988-11-22 | 1990-05-31 | Sapporo Breweries Ltd | 光学活性アルコールの製造方法 |
JPH06237790A (ja) * | 1992-12-21 | 1994-08-30 | Duphar Internatl Res Bv | ヘテロ−二環式アルコールエナンチオマーの酵素による立体選択的製造方法 |
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Publication number | Priority date | Publication date | Assignee | Title |
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WO2010123067A1 (ja) * | 2009-04-23 | 2010-10-28 | 株式会社カネカ | (s)-1-置換プロパン-1-オール誘導体の製造方法 |
JP5704650B2 (ja) * | 2009-04-23 | 2015-04-22 | 株式会社カネカ | (s)−1−置換プロパン−1−オール誘導体の製造方法 |
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EP1713788B1 (de) | 2009-03-04 |
ES2320354T3 (es) | 2009-05-21 |
DK1713788T3 (da) | 2009-06-08 |
US20070128704A1 (en) | 2007-06-07 |
DE102004004719A1 (de) | 2005-08-18 |
PT1713788E (pt) | 2009-03-31 |
EP1713788A1 (de) | 2006-10-25 |
CN1914190A (zh) | 2007-02-14 |
US7435835B2 (en) | 2008-10-14 |
CN100491369C (zh) | 2009-05-27 |
DE502005006744D1 (de) | 2009-04-16 |
WO2005073215A1 (de) | 2005-08-11 |
ATE424392T1 (de) | 2009-03-15 |
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