JP4923630B2 - Method for producing 4-substituted tetrahydropyran - Google Patents
Method for producing 4-substituted tetrahydropyran Download PDFInfo
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Description
本発明は、4-置換テトラヒドロピラン-4-カルボン酸から4-置換テトラヒドロピランを製造する方法に関する。4-置換テトラヒドロピラン（4-シアノテトラヒドロピラン、テトラヒドロピラン-4-カルボン酸）は、医薬・農薬等の原料や合成中間体として有用な化合物である。 The present invention relates to a process for producing 4-substituted tetrahydropyran from 4-substituted tetrahydropyran-4-carboxylic acid. 4-Substituted tetrahydropyran (4-cyanotetrahydropyran, tetrahydropyran-4-carboxylic acid) is a useful compound as a raw material for pharmaceuticals, agricultural chemicals, and synthetic intermediates.
従来、4-置換テトラヒドロピラン-4-カルボン酸から4-置換テトラヒドロピランを製造する方法としては、例えば、4-シアノテトラヒドロピラン-4-カルボン酸を180〜200℃に加熱して、単離収率66％で4-シアノテトラヒドロピランを得る方法が知られている（例えば、非特許文献１参照）。また、テトラヒドロピラン-4,4-ジカルボン酸を180℃に加熱して、単離収率85％でテトラヒドロピラン-4-カルボン酸を得る方法が知られている（例えば、非特許文献２参照）。しかしながら、上記いずれの方法においても高い反応温度が必要である上に、収率が低く、4-置換テトラヒドロピランの工業的な製法としては満足するものではなかった。 Conventionally, as a method for producing 4-substituted tetrahydropyran from 4-substituted tetrahydropyran-4-carboxylic acid, for example, 4-cyanotetrahydropyran-4-carboxylic acid is heated to 180 to 200 ° C. and isolated. A method for obtaining 4-cyanotetrahydropyran at a rate of 66% is known (for example, see Non-Patent Document 1). Further, a method is known in which tetrahydropyran-4,4-dicarboxylic acid is heated to 180 ° C. to obtain tetrahydropyran-4-carboxylic acid in an isolated yield of 85% (see, for example, Non-Patent Document 2). . However, in any of the above methods, a high reaction temperature is required and the yield is low, which is not satisfactory as an industrial production method of 4-substituted tetrahydropyran.
本発明の課題は、即ち、上記問題点を解決し、温和な条件下、簡便な方法によって、4-置換テトラヒドロピラン-4-カルボン酸から4-置換テトラヒドロピランを高収率で製造出来る、工業的に好適な4-置換テトラヒドロピランの製造方法を提供することである。 An object of the present invention is to solve the above-mentioned problems, and can produce 4-substituted tetrahydropyran from 4-substituted tetrahydropyran-4-carboxylic acid in a high yield by a simple method under mild conditions. It is intended to provide a method for producing a particularly preferred 4-substituted tetrahydropyran.
本発明の課題は、一般式（１） The subject of this invention is general formula (1).
（式中、Ｒは、シアノ基又はカルボキシル基を示す。）
で示される4-置換テトラヒドロピラン-4-カルボン酸と有機アミンとを反応させることを特徴とする、式（２）
(In the formula, R represents a cyano group or a carboxyl group.)
Wherein the 4-substituted tetrahydropyran-4-carboxylic acid represented by the formula (2) is reacted with an organic amine.
（式中、Ｒは、前記と同義である。）
で示される4-置換テトラヒドロピランの製造方法によって解決される。
(In the formula, R is as defined above.)
It is solved by the method for producing 4-substituted tetrahydropyran represented by the following formula.
本発明により、温和な条件下、簡便な方法によって、4-置換テトラヒドロピラン-4-カルボン酸から4-置換テトラヒドロピランを高収率で製造出来る、工業的に好適な4-置換テトラヒドロピランの製造方法を提供することが出来る。 INDUSTRIAL APPLICABILITY According to the present invention, an industrially suitable 4-substituted tetrahydropyran can be produced from 4-substituted tetrahydropyran-4-carboxylic acid in a high yield by a simple method under mild conditions. A method can be provided.
本発明の反応において使用する4-置換テトラヒドロピラン-4-カルボン酸は、前記の一般式（１）で示される。その一般式（１）において、Ｒは、シアノ基又はカルボキシル基を示す。 The 4-substituted tetrahydropyran-4-carboxylic acid used in the reaction of the present invention is represented by the above general formula (1). In the general formula (1), R represents a cyano group or a carboxyl group.
本発明の反応において使用する有機塩基とは、例えば、ジエチルアミン、トリエチルアミン、ジ-n-プロピルアミン、ジイソプロピルアミン、トリ-n-プロピルアミン、トリイソプロピルアミン、ジ-n-ブチルアミン、ジイソブチルアミン、トリ-n-ブチルアミン、トリイソブチルアミン、エチルイソプロピルアミン、ジイソプロピルメチルアミン、ジイソプロピルエチルアミン、ジ-n-ペンチルアミン、ジイソペンチルアミン、ジシクロヘプチルアミン、トリ-n-ペンチルアミン、トリイソペンチルアミン、ジ-n-ヘキシルアミン、ジイソヘキシルアミン、ジシクロヘキシルアミン、トリ-n-ヘキシルアミン、トリイソヘキシルアミン、ジ-n-ヘプチルアミン、ジイソヘプチルアミン、トリ-n-ヘプチルアミン、トリイソヘプチルアミン、ジ-n-オクチルアミン、ジイソオクチルアミン、トリ-n-オクチルアミン、トリイソオクチルアミン、ジ-n-ノニルアミン、ジイソノニルアミン、トリ-n-ノニルアミン、トリイソノニルアミン、ジ-n-デシルアミン、ジイソデシルアミン、トリ-n-デシルアミン、トリイソデシルアミン、1,8-ジアザビシクロ[5,4,0]-7-ウンデセン、ジアザジシクロ[2,2,2]オクタン等のアルキルアミン類；メチルベンジルアミン、ジメチルベンジルアミン、エチルベンジルアミン、ジエチルベンジルアミン等のベンジルアミン類；メチルアニリン、ジメチルアニリン、エチルアニリン、ジエチルアニリン等のアニリン類；ピリジン、メチルピリジン、ジメチルアミノピリジン等のピリジン類；キノリン、イソキノリン等のキノリン類が挙げられるが、好ましくはアルキルアミン類、更に好ましくはトリエチルアミン、ジ-n-ブチルアミン、トリ-n-ブチルアミン、トリ-n-オクチルアミンが使用される。なお、これらの有機塩基は、単独又は二種以上を混合して使用しても良い。 The organic base used in the reaction of the present invention includes, for example, diethylamine, triethylamine, di-n-propylamine, diisopropylamine, tri-n-propylamine, triisopropylamine, di-n-butylamine, diisobutylamine, tri- n-butylamine, triisobutylamine, ethylisopropylamine, diisopropylmethylamine, diisopropylethylamine, di-n-pentylamine, diisopentylamine, dicycloheptylamine, tri-n-pentylamine, triisopentylamine, di- n-hexylamine, diisohexylamine, dicyclohexylamine, tri-n-hexylamine, triisohexylamine, di-n-heptylamine, diisoheptylamine, tri-n-heptylamine, triisoheptylamine, di -n-octylamine, Isooctylamine, tri-n-octylamine, triisooctylamine, di-n-nonylamine, diisononylamine, tri-n-nonylamine, triisononylamine, di-n-decylamine, diisodecylamine, tri-n-decylamine Alkylamines such as triisodecylamine, 1,8-diazabicyclo [5,4,0] -7-undecene, diazadicyclo [2,2,2] octane; methylbenzylamine, dimethylbenzylamine, ethylbenzylamine, Benzylamines such as diethylbenzylamine; anilines such as methylaniline, dimethylaniline, ethylaniline and diethylaniline; pyridines such as pyridine, methylpyridine and dimethylaminopyridine; and quinolines such as quinoline and isoquinoline, Preferably alkylamines, more preferably Ethylamine, di -n- butylamine, tri -n- butylamine, tri -n- octylamine is used. In addition, you may use these organic bases individually or in mixture of 2 or more types.
前記有機塩基の使用量は、4-置換テトラヒドロピラン-4-カルボン酸1ｇに対して、好ましくは0.01〜100ml、更に好ましくは0.05〜50ml、特に好ましくは0.1〜5.0mlである。 The amount of the organic base used is preferably 0.01 to 100 ml, more preferably 0.05 to 50 ml, particularly preferably 0.1 to 5.0 ml with respect to 1 g of 4-substituted tetrahydropyran-4-carboxylic acid.
本発明の反応は溶媒中の存在下又は非存在下にて行われる。使用する溶媒としては、反応を阻害しないものならば特に限定されず、例えば、水；N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、N-メチルピロリドン等のアミド類；N,N'-ジメチルイミダゾリジノン等の尿素類；ジメチルスルホキシド、スルホラン等のスルホキシド類；n-プロピルアルコール、n-ブチルアルコール等のアルコール類；ジイソプロピルエーテル、ジオキサン、シクロプロピルメチルエーテル等のエーテル類；トルエン、キシレン等の芳香族炭化水素類；酢酸エチル、酢酸ブチル等の酢酸エステル類；アセトニトリル、プロピオニトリル等のニトリル類が挙げられるが、好ましくはアミド類、スルホキシド類、或いはそれらと芳香族炭化水素類又は酢酸エステル類との混合溶媒、更に好ましくはN,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、N-メチルピロリドン、N,N'-ジメチルイミダゾリジノン、ジメチルスルホキシド、或いはそれらとトルエン、酢酸エチル又は酢酸ブチル、水との混合溶媒が使用される。なお、これらの溶媒は、単独又は二種以上を混合して使用しても良い。 The reaction of the present invention is carried out in the presence or absence of a solvent. The solvent to be used is not particularly limited as long as it does not inhibit the reaction. For example, water; amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone; N, N′— Ureas such as dimethylimidazolidinone; Sulfoxides such as dimethyl sulfoxide and sulfolane; Alcohols such as n-propyl alcohol and n-butyl alcohol; Ethers such as diisopropyl ether, dioxane and cyclopropyl methyl ether; Toluene, xylene and the like Aromatic hydrocarbons; acetates such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and propionitrile, preferably amides, sulfoxides, and aromatic hydrocarbons or acetic acid Mixed solvent with esters, more preferably N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, N, N′-dimethylimidazolidinone, dimethyl sulfoxide, or a mixed solvent thereof with toluene, ethyl acetate or butyl acetate and water is used. In addition, you may use these solvents individually or in mixture of 2 or more types.
前記溶媒の使用量は、反応液の均一性や攪拌性により適宜調節するが、4-置換テトラヒドロピラン-4-カルボン酸1gに対して、好ましくは0〜100ml、更に好ましくは0〜50ml、特に好ましくは0〜10mlである。 The amount of the solvent used is appropriately adjusted depending on the homogeneity and stirrability of the reaction solution, but is preferably 0 to 100 ml, more preferably 0 to 50 ml, especially 1 to 4 g of 4-substituted tetrahydropyran-4-carboxylic acid. Preferably it is 0-10 ml.
本発明の反応は、例えば、4-置換テトラヒドロピラン-4-カルボン酸、有機塩基及び溶媒を混合して、攪拌しながら反応させる等の方法によって行われる。その際の反応温度は、好ましくは50〜150℃、更に好ましくは80〜130℃であり、反応圧力は特に制限されない。 The reaction of the present invention is performed by, for example, a method of mixing 4-substituted tetrahydropyran-4-carboxylic acid, an organic base and a solvent and reacting them with stirring. The reaction temperature at that time is preferably 50 to 150 ° C., more preferably 80 to 130 ° C., and the reaction pressure is not particularly limited.
なお、最終生成物である4-置換テトラヒドロピランは、例えば、反応終了後、濾過、濃縮、蒸留、再結晶、カラムクロマトグラフィー等の一般的な方法によって単離・精製される。 The final product, 4-substituted tetrahydropyran, is isolated and purified by a general method such as filtration, concentration, distillation, recrystallization, column chromatography after completion of the reaction.
次に、実施例を挙げて本発明を具体的に説明するが、本発明の範囲はこれらに限定されるものではない。 Next, the present invention will be specifically described with reference to examples, but the scope of the present invention is not limited thereto.
実施例１（4-シアノテトラヒドロピランの合成）
攪拌装置、温度計及び還流冷却器を備えた内容積25mlのガラス製フラスコに、4-シアノテトラヒドロピラン-4-カルボン酸1.0g(6.445mmol)、トリ-n-ブチルアミン1.0ml及びN,N-ジメチルホルムアミド2.0mlを加え、攪拌しながら120℃で5時間反応させた。反応終了後、反応液をガスクロマトグラフィーで分析（内部標準法）したところ、4-シアノテトラヒドロピランが0.702g生成していた（反応収率；97.9％）。
Example 1 (Synthesis of 4-cyanotetrahydropyran)
Into a glass flask equipped with a stirrer, a thermometer and a reflux condenser and having an internal volume of 25 ml, 1.0 g (6.445 mmol) of 4-cyanotetrahydropyran-4-carboxylic acid, 1.0 ml of tri-n-butylamine and N, N- Dimethylformamide (2.0 ml) was added, and the mixture was reacted at 120 ° C. for 5 hours with stirring. After completion of the reaction, the reaction solution was analyzed by gas chromatography (internal standard method). As a result, 0.702 g of 4-cyanotetrahydropyran was formed (reaction yield; 97.9%).
実施例２（4-シアノテトラヒドロピランの合成）
攪拌装置、温度計及び還流冷却器を備えた内容積25mlのガラス製フラスコに、4-シアノテトラヒドロピラン-4-カルボン酸1.0g(6.445mmol)、ジ-n-ブチルアミン1.0ml及びN,N-ジメチルホルムアミド2.0mlを加え、攪拌しながら120℃で5時間反応させた。反応終了後、反応液をガスクロマトグラフィーで分析（内部標準法）したところ、4-シアノテトラヒドロピランが0.653g生成していた（反応収率；91.2％）。
Example 2 (Synthesis of 4-cyanotetrahydropyran)
Into a glass flask equipped with a stirrer, a thermometer and a reflux condenser and having an internal volume of 25 ml, 1.0 g (6.445 mmol) of 4-cyanotetrahydropyran-4-carboxylic acid, 1.0 ml of di-n-butylamine and N, N- Dimethylformamide (2.0 ml) was added, and the mixture was reacted at 120 ° C. for 5 hours with stirring. After completion of the reaction, the reaction mixture was analyzed by gas chromatography (internal standard method). As a result, 0.653 g of 4-cyanotetrahydropyran was formed (reaction yield; 91.2%).
実施例３（4-シアノテトラヒドロピランの合成）
攪拌装置、温度計及び還流冷却器を備えた内容積25mlのガラス製フラスコに、4-シアノテトラヒドロピラン-4-カルボン酸1.0g(6.445mmol)、ジ-n-ブチルアミン1.0ml及びN,N-ジメチルホルムアミド2.0mlを加え、攪拌しながら120℃で5時間反応させた。反応終了後、反応液をガスクロマトグラフィーで分析（内部標準法）したところ、4-シアノテトラヒドロピランが0.645g生成していた（反応収率；90.0％）。
Example 3 (Synthesis of 4-cyanotetrahydropyran)
Into a glass flask equipped with a stirrer, a thermometer and a reflux condenser and having an internal volume of 25 ml, 1.0 g (6.445 mmol) of 4-cyanotetrahydropyran-4-carboxylic acid, 1.0 ml of di-n-butylamine and N, N- Dimethylformamide (2.0 ml) was added, and the mixture was reacted at 120 ° C. for 5 hours with stirring. After completion of the reaction, the reaction solution was analyzed by gas chromatography (internal standard method). As a result, 0.645 g of 4-cyanotetrahydropyran was formed (reaction yield; 90.0%).
実施例４（4-シアノテトラヒドロピランの合成）
攪拌装置、温度計及び還流冷却器を備えた内容積25mLのガラス製フラスコに、4-シアノテトラヒドロピラン-4-カルボン酸1.0g(6.445mmol)及びトリ-n-ブチルアミン5.0mlを加え、攪拌しながら120℃で5時間反応させた。反応終了後、反応液をガスクロマトグラフィーで分析（内部標準法）したところ、4-シアノテトラヒドロピランが0.642g生成していた（反応収率；89.6％）。
Example 4 (Synthesis of 4-cyanotetrahydropyran)
To a glass flask having an internal volume of 25 mL equipped with a stirrer, a thermometer and a reflux condenser, 1.0 g (6.445 mmol) of 4-cyanotetrahydropyran-4-carboxylic acid and 5.0 ml of tri-n-butylamine were added and stirred. The reaction was carried out at 120 ° C. for 5 hours. After completion of the reaction, the reaction solution was analyzed by gas chromatography (internal standard method). As a result, 0.642 g of 4-cyanotetrahydropyran was formed (reaction yield; 89.6%).
実施例５（4-シアノテトラヒドロピランの合成）
攪拌装置、温度計及び還流冷却器を備えた内容積25mlのガラス製フラスコに、4-シアノテトラヒドロピラン-4-カルボン酸1.0g(6.445mmol)及びトリ-n-オクチルアミン5.0mlを加え、攪拌しながら120℃で5時間反応させた。反応終了後、反応液をガスクロマトグラフィーで分析（内部標準法）したところ、4-シアノテトラヒドロピランが0.688g生成していた（反応収率；96.0％）。
Example 5 (Synthesis of 4-cyanotetrahydropyran)
To a glass flask having an internal volume of 25 ml equipped with a stirrer, a thermometer and a reflux condenser, 1.0 g (6.445 mmol) of 4-cyanotetrahydropyran-4-carboxylic acid and 5.0 ml of tri-n-octylamine were added and stirred. The reaction was carried out at 120 ° C. for 5 hours. After completion of the reaction, the reaction solution was analyzed by gas chromatography (internal standard method). As a result, 0.688 g of 4-cyanotetrahydropyran was formed (reaction yield; 96.0%).
実施例６（4-シアノテトラヒドロピランの合成）
攪拌装置、温度計及び還流冷却器を備えた内容積25mlのガラス製フラスコに、4-シアノテトラヒドロピラン-4-カルボン酸1.0g(6.445mmol)、ピリジン1.0ml及びN,N-ジメチルホルムアミド2.0mlを加え、攪拌しながら120℃で5時間反応させた。反応終了後、反応液をガスクロマトグラフィーで分析（内部標準法）したところ、4-シアノテトラヒドロピランが0.454g生成していた（反応収率；63.4％）。
Example 6 (Synthesis of 4-cyanotetrahydropyran)
To a glass flask having an internal volume of 25 ml equipped with a stirrer, a thermometer and a reflux condenser, 1.0 g (6.445 mmol) of 4-cyanotetrahydropyran-4-carboxylic acid, 1.0 ml of pyridine and 2.0 ml of N, N-dimethylformamide Was allowed to react at 120 ° C. for 5 hours with stirring. After completion of the reaction, the reaction solution was analyzed by gas chromatography (internal standard method). As a result, 0.454 g of 4-cyanotetrahydropyran was formed (reaction yield; 63.4%).
実施例７（テトラヒドロピラン-4-カルボン酸の合成）
攪拌装置、温度計及び還流冷却器を備えた内容積25mlのガラス製フラスコに、テトラヒドロピラン-4,4-ジカルボン酸0.50g(2.871mmol)及びトリ-n-ブチルアミン1.5mlを加え、攪拌しながら100℃で3時間反応させた。反応終了後、反応液をガスクロマトグラフィーで分析（内部標準法）したところ、テトラヒドロピラン-4-カルボン酸が0.304g生成していた（反応収率；81.4％）。
Example 7 (Synthesis of tetrahydropyran-4-carboxylic acid)
To a glass flask having an internal volume of 25 ml equipped with a stirrer, a thermometer and a reflux condenser, 0.50 g (2.871 mmol) of tetrahydropyran-4,4-dicarboxylic acid and 1.5 ml of tri-n-butylamine were added and stirred. The reaction was carried out at 100 ° C. for 3 hours. After completion of the reaction, the reaction mixture was analyzed by gas chromatography (internal standard method). As a result, 0.304 g of tetrahydropyran-4-carboxylic acid was produced (reaction yield; 81.4%).
実施例８（テトラヒドロピラン-4-カルボン酸の合成）
攪拌装置、温度計及び還流冷却器を備えた内容積25mlのガラス製フラスコに、テトラヒドロピラン-4,4-ジカルボン酸0.50g(2.871mmol)、トリ-n-オクチルアミン0.5ml及びN,N-ジメチルホルムアミド1.0mlを加え、攪拌しながら100℃で3時間反応させた。反応終了後、反応液をガスクロマトグラフィーで分析（内部標準法）したところ、テトラヒドロピラン-4-カルボン酸が0.315g生成していた（反応収率；84.2％）。
Example 8 (Synthesis of tetrahydropyran-4-carboxylic acid)
A glass flask having an internal volume of 25 ml equipped with a stirrer, a thermometer and a reflux condenser was charged with 0.50 g (2.871 mmol) of tetrahydropyran-4,4-dicarboxylic acid, 0.5 ml of tri-n-octylamine and N, N- 1.0 ml of dimethylformamide was added and reacted at 100 ° C. for 3 hours with stirring. After completion of the reaction, the reaction solution was analyzed by gas chromatography (internal standard method). As a result, 0.315 g of tetrahydropyran-4-carboxylic acid was produced (reaction yield; 84.2%).
本発明は、4-置換テトラヒドロピラン-4-カルボン酸から4-置換テトラヒドロピランを製造する方法に関する。4-置換テトラヒドロピラン（4-シアノテトラヒドロピラン、テトラヒドロピラン-4-カルボン酸）は、医薬・農薬等の原料や合成中間体として有用な化合物である。 The present invention relates to a process for producing 4-substituted tetrahydropyran from 4-substituted tetrahydropyran-4-carboxylic acid. 4-Substituted tetrahydropyran (4-cyanotetrahydropyran, tetrahydropyran-4-carboxylic acid) is a useful compound as a raw material for pharmaceuticals, agricultural chemicals, and synthetic intermediates.
Claims (4)
で示される4-置換テトラヒドロピラン-4-カルボン酸とアルキルアミン類、ベンジルアミン類、及びアニリン類から選ばれる単独又は二種以上の有機塩基とを反応させることを特徴とする、式（２）
で示される4-置換テトラヒドロピランの製造方法。 General formula (1)
A 4-substituted tetrahydropyran-4-carboxylic acid represented by the formula (2) is reacted with one or more organic bases selected from alkylamines, benzylamines, and anilines.
The manufacturing method of 4-substituted tetrahydropyran shown by these.
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