JP5806739B2 - β−官能化脂肪族エステルの製造方法 - Google Patents
β−官能化脂肪族エステルの製造方法 Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
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- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/12—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of acyclic carbon skeletons
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/14—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of carbon skeletons containing rings
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- 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
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Description
に示されるβ-官能化カルボン酸エステルの製造方法であって、一般式(II):
に示される不飽和エステルを、式(III):
に示されるホウ素化合物、またはアミン
R'''-NH-R'''' (IV)
[式中、R'''およびR''''は上記と同じ意味である]
のいずれか及びロジウム含有触媒の存在下に、80〜120℃の間の温度で、溶媒中、酸素不含雰囲気下、ワンポットで反応させることを特徴とする、方法に関する。
テフロンコートした撹拌子と乾燥セプタムを含むオーブン乾燥ガラス器中、窒素雰囲気下で、反応を行なった。反応媒体から大気中の酸素を取り除くために、反応剤を混合する前に、45分間のアルゴン散布によって溶媒を脱気した。溶媒は、使用に先立って標準手順によって精製した。n−ドデカンを内部標準として用い、GCによって全反応をモニターした。n−ドデカンに関する生成物のレスポンスファクターは、物質の既知量を分析することによって実験的に得た。GC分析は、HP-5キャピラリーカラム(フェニルメチルシロキサン30m×320×0.25、100/2.3-30-300/3)、および60℃、2分で開始後、300℃まで30℃/分の傾斜、その後この温度で3分間保持する時間プログラムを使用して行なった。カラムクロマトグラフィは、Combi Flash Companion-Chromatography-System (Isco-Systems)およびRediSep充填カラム(12g)を使用して行なった。TLC分析は、市販の60 F254シリカゲルプレートについて行なった。NMRスペクトルは、Bruker AMX 200、AMX 400、あるいはBruker Avance 600システム上で、溶媒としてCDCl3を用い、200、400あるいは600MHzおよび51、101あるいは151MHzにおけるプロトンと炭素のそれぞれの共鳴について得た。質量スペクトルのデータは、GC-MS Saturn 2100 T (Varian)によって得た。別段の記載をしない限り、市販の基材をそのまま使用した。非市販品のオレフィンエステル1を、対応する酸から標準エステル化法を用いて合成した。
オーブン乾燥した20mLのクリンプトップバイアルに、アセチルアセトナト(1,5-シクロオクタジエン)ロジウム(I)(1.5モル%)、ビフェホス(1.5モル%)、ホウ酸アリール(2.0当量)および撹拌子を充填し、またテフロンセプタムでシールし、アルゴンで3回真空パージした。続いて、トルエン(3mL/mmolエステル)、オレフィンエステル1(0.5-1.0 mmol)および水(150μL/mmolエステル)を、皮下注射器によって添加し、反応混合物を100℃で20時間撹拌した。室温(=21℃)に冷却後、溶媒を真空で除去し、フラッシュカラムクロマトグラフィ(SiO2、酢酸エチル−ヘキサンあるいはジエチルエーテル−ヘキサン)の後にエステル3を得た。
13C NMR (101 MHz, CDCl 3) 172.3, 144.1, 128.3, 127.4, 126.3, 60.1, 41.9, 41.8, 38.4, 20.4, 14.0, 13.9 ppm。
MS (Ion trap, EI): m/z (%) = 221 [M+] (86), 174 (55), 135 (68), 132 (92), 118 (37), 105 (27), 91 (100)。
本明細書の当初の開示は以下を包含する。
〔1〕 式(I):
に示されるβ-官能化カルボン酸エステルの製造方法であって、一般式(II):
に示される不飽和エステルを、式(III):
に示されるホウ素化合物、またはアミン
R'''-NH-R'''' (IV)
[式中、R'''およびR''''は上記と同じ意味である]
のいずれか及びロジウム含有触媒の存在下に、80〜120℃の間の温度で、溶媒中、酸素不含雰囲気下、ワンポットで反応させることを特徴とする、方法。
〔2〕 式(II):
[式中、R'は水素原子を表わし、Rはエチル基である]
による基材を選択することを特徴とする、〔1〕に記載の方法。
〔3〕 ロジウム含有触媒は、Rh原子を含み酸化数+1を有するRh複合体から選択されることを特徴とする、〔1〕〜〔2〕のいずれかに記載の方法。
〔4〕 ロジウム含有触媒は、(i)Rh(acac)(COD)、[Rh(OH)(COD)] 2 または[Rh(Cl)(COD)] 2 と、(ii)ビフェホスあるいはP(Oアリル) 3 配位子とを、(i):(ii)が2:1乃至1:2、好ましくは1:1のモル量で選択することを特徴とする、〔1〕〜〔3〕のいずれかに記載の方法。
〔5〕 溶媒は、ベンゼン、トルエン、クロロベンゼン、ジフェニルエーテルあるいは水とこれらのブレンドから選択されることを特徴とする、〔1〕〜〔4〕のいずれかに記載の方法。
〔6〕 溶媒は、トルエン、あるいは水およびトルエンの重量比1:25〜1:10、好ましくは1:20のブレンドから選択されることを特徴とする、〔4〕に記載の方法。
〔7〕 式(III)に示されるトリアリールホウ素化合物は、PhB(OH) 2 , PhB(pin), PhBMIDAエステル, PhBF 3 K, KB(4-ClC 6 H 4 ) 4 , NaB(2-ナフチル) 4 , NaB(4-トリル) 4 , およびKB(2-チエニル) 4 からなる群から選択されることを特徴とする、〔1〕〜〔6〕のいずれかに記載の方法。
Claims (6)
- 式(I):
に示されるβ-官能化カルボン酸エステルの製造方法であって、一般式(II):
に示される不飽和エステルを、式(III):
に示されるホウ素化合物、またはアミン
R'''-NH-R'''' (IV)
[式中、R'''およびR''''は上記と同じ意味である]
のいずれか及びRh(acac)(COD)及び[Rh(Cl)(COD)] 2 からなる群から選択されるロジウム含有触媒ならびにビフェホスの存在下に、80〜120℃の間の温度で、溶媒中、酸素不含雰囲気下、ワンポットで反応させることを特徴とする、方法。 - 式(II):
[式中、R'は水素原子を表わし、Rはエチル基である]
による基材を選択することを特徴とする、請求項1に記載の方法。 - ロジウム含有触媒は、(i)Rh(acac)(COD)または[Rh(Cl)(COD)]2と、(ii)ビフェホスとを、(i):(ii)が2:1乃至1:2のモル量で選択することを特徴とする、請求項1〜2のいずれかに記載の方法。
- 溶媒は、ベンゼン、トルエン、クロロベンゼン、ジフェニルエーテルあるいは水とこれらのブレンドから選択されることを特徴とする、請求項1〜3のいずれかに記載の方法。
- 溶媒は、トルエン、あるいは水およびトルエンの重量比1:25〜1:10のブレンドから選択されることを特徴とする、請求項3に記載の方法。
- 式(III)に示されるホウ素化合物は、NaB(4-トリル) 4 およびNaBPh 4 からなる群から選択されることを特徴とする、請求項1〜5のいずれかに記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP10189314A EP2447245A1 (en) | 2010-10-28 | 2010-10-28 | A method to prepare beta-functionalized aliphatic esters |
EPEP10189314 | 2010-10-28 | ||
PCT/EP2011/004400 WO2012055455A1 (en) | 2010-10-28 | 2011-08-31 | A method to prepare beta - functionalized aliphatic esters |
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JP2014505013A JP2014505013A (ja) | 2014-02-27 |
JP2014505013A5 JP2014505013A5 (ja) | 2014-10-09 |
JP5806739B2 true JP5806739B2 (ja) | 2015-11-10 |
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JP2013535285A Active JP5806739B2 (ja) | 2010-10-28 | 2011-08-31 | β−官能化脂肪族エステルの製造方法 |
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US (1) | US8877958B2 (ja) |
EP (2) | EP2447245A1 (ja) |
JP (1) | JP5806739B2 (ja) |
KR (1) | KR101872044B1 (ja) |
CN (1) | CN103180287B (ja) |
AU (1) | AU2011323015B2 (ja) |
BR (1) | BR112013010216A2 (ja) |
CA (1) | CA2815907A1 (ja) |
ES (1) | ES2648140T3 (ja) |
MX (1) | MX338234B (ja) |
WO (1) | WO2012055455A1 (ja) |
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DE102018215394A1 (de) * | 2018-09-11 | 2020-03-12 | Rheinisch-Westfälische Technische Hochschule Aachen | Verfahren zur chemischen Umsetzung von Zuckern oder Zuckeralkoholen zu Glykolen |
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JP4183153B2 (ja) * | 1999-08-26 | 2008-11-19 | 三菱レイヨン株式会社 | 光学活性β−アリールエステル化合物及びアミド化合物の合成法 |
TW200804269A (en) * | 2005-11-16 | 2008-01-16 | Astrazeneca Ab | Chemical process |
-
2010
- 2010-10-28 EP EP10189314A patent/EP2447245A1/en not_active Withdrawn
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2011
- 2011-08-31 EP EP11752123.7A patent/EP2632888B1/en active Active
- 2011-08-31 WO PCT/EP2011/004400 patent/WO2012055455A1/en active Application Filing
- 2011-08-31 CA CA2815907A patent/CA2815907A1/en not_active Abandoned
- 2011-08-31 MX MX2013004682A patent/MX338234B/es active IP Right Grant
- 2011-08-31 ES ES11752123.7T patent/ES2648140T3/es active Active
- 2011-08-31 BR BR112013010216A patent/BR112013010216A2/pt active Search and Examination
- 2011-08-31 AU AU2011323015A patent/AU2011323015B2/en active Active
- 2011-08-31 CN CN201180051767.1A patent/CN103180287B/zh active Active
- 2011-08-31 KR KR1020137010737A patent/KR101872044B1/ko active IP Right Grant
- 2011-08-31 JP JP2013535285A patent/JP5806739B2/ja active Active
- 2011-08-31 US US13/881,853 patent/US8877958B2/en active Active
Also Published As
Publication number | Publication date |
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BR112013010216A2 (pt) | 2016-09-13 |
AU2011323015B2 (en) | 2016-06-09 |
WO2012055455A1 (en) | 2012-05-03 |
ES2648140T3 (es) | 2017-12-28 |
KR20130126902A (ko) | 2013-11-21 |
JP2014505013A (ja) | 2014-02-27 |
CN103180287A (zh) | 2013-06-26 |
EP2632888A1 (en) | 2013-09-04 |
MX338234B (es) | 2016-04-08 |
CN103180287B (zh) | 2016-01-13 |
EP2447245A1 (en) | 2012-05-02 |
MX2013004682A (es) | 2013-05-17 |
AU2011323015A1 (en) | 2013-05-23 |
RU2013124073A (ru) | 2014-12-10 |
US20130225852A1 (en) | 2013-08-29 |
US8877958B2 (en) | 2014-11-04 |
KR101872044B1 (ko) | 2018-06-27 |
EP2632888B1 (en) | 2017-08-23 |
CA2815907A1 (en) | 2012-05-03 |
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