JPH0441479A - Production of 3-(4-1-imidazolylmethyl)phenyl)-2-propene-1-ol - Google Patents

Production of 3-(4-1-imidazolylmethyl)phenyl)-2-propene-1-ol

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Publication number
JPH0441479A
JPH0441479A JP2148534A JP14853490A JPH0441479A JP H0441479 A JPH0441479 A JP H0441479A JP 2148534 A JP2148534 A JP 2148534A JP 14853490 A JP14853490 A JP 14853490A JP H0441479 A JPH0441479 A JP H0441479A
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JP
Japan
Prior art keywords
formula
compound shown
imidazolylmethyl
compound
phenyl
Prior art date
Legal status (The legal status 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 status listed.)
Pending
Application number
JP2148534A
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Japanese (ja)
Inventor
Hiroshi Ikawa
伊川　博
Akihito Kakuiri
角入　章仁
Yasuko Konagai
小長井　靖子
Yasuo Sekine
関根　安男
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Fujirebio Inc
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Fujirebio Inc
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Filing date
Publication date
Application filed by Fujirebio Inc filed Critical Fujirebio Inc
Priority to JP2148534A priority Critical patent/JPH0441479A/en
Publication of JPH0441479A publication Critical patent/JPH0441479A/en
Pending legal-status Critical Current

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    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

PURPOSE:To obtain the title compound by simple operations advantageously, by reacting a 1-halogeno-4-(1-imidazolylmethyl)benzene with a propargyl alcohol in the presence of a catalyst, reducing the prepared reaction product and further deprotecting. CONSTITUTION:A compound shown by formula III (X is halogen) is reacted with a compound shown by formula IV (Y is H, Ni or Cu; R is H or OH- protecting group) in the presence of a base and a catalyst to give a compound shown by formula I. Then, the compound is reduced to give a compound shown by formula VI, which is further deprotected to give the objective compound shown by formula II having both vasodilating action and inhibitory action on aggregation of blood platelet based on calcium antagonism under a mild condition by simple reaction operations by a method suitable for industrial mass production without using a dangerous reagent. The compound shown by formula III is readily produced from a compound shown by formula V (Z is halogen, methanesulfonyl or p-toluenesulfonyl) and imidazole.

Description

【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、３−　（４−（１−イミダゾリルメチル）フ
ェニルツー２−プロペン−１−オールの製造方法に関す
る。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a method for producing 3-(4-(1-imidazolylmethyl)phenyl-2-propen-1-ol).

前記の化合物は、カルシウム拮抗作用に基づく血管拡張
作用と血小板凝集抑制作用を有する化合物に誘導するこ
とができる（特願平１−２５０３７５参照）。The above-mentioned compounds can be induced into compounds having vasodilating action and platelet aggregation inhibiting action based on calcium antagonistic action (see Japanese Patent Application No. 1-250375).

〔従来の技術〕[Conventional technology]

従来３−　（４−（１−イミダゾリルメチル）フェニル
〕〜２−プロペンー１−オールを製ａｔ　る方法として
は、４−（１−イミダゾリルメチル）桂皮酸エチルエス
テルを水素化リチウムアルミニウムなどを用いて還元す
る方法が知られている（特開昭６１１９７５７８）。The conventional method for producing 3-(4-(1-imidazolylmethyl)phenyl]~2-propene-1-ol is to prepare ethyl 4-(1-imidazolylmethyl)cinnamate using lithium aluminum hydride or the like. A method of reduction is known (Japanese Patent Application Laid-Open No. 61197578).

〔発明が解決しようとする問題点〕[Problem that the invention seeks to solve]

しかしながら、従来の方法は、水素化リチウムアルミニ
ウムを大量に用いなければならず、反応操作自体もさる
ことながら、後処理操作に際し、細心の注意を要する、
等の欠点を有する。However, the conventional method requires the use of a large amount of lithium aluminum hydride, and requires careful attention not only in the reaction operation itself but also in the post-treatment operation.
It has the following disadvantages.

〔問題点を解決するための手段〕[Means for solving problems]

本発明者らは、従来方法の欠点を克服すべく検討した結
果、穏和な条件下、危険を伴う試薬などを用いずに、４
−　（３−（１−イミダゾリルメチル）フェニル〕−２
−プロペンー１−オールヲ製造する方法を完成したもの
である。As a result of studies to overcome the shortcomings of conventional methods, the present inventors have discovered that 4
- (3-(1-imidazolylmethyl)phenyl)-2
- A method for producing propene-1-ol has been completed.

本発明は、以下の式により表すことが出来る。The present invention can be expressed by the following formula.

〔第一工程〕 本工程は、前記式［Ｉ（Ｉ）で表される化合物と前記式
［ＩＶ）で表される化合物とを塩基と触媒の存在下反応
させることにより、前記式〔Ｉ〕で表される化合物を製
造するものである。[First step] In this step, the compound represented by the above formula [I (I) and the compound represented by the above formula [IV] are reacted in the presence of a base and a catalyst to form the above formula [I]. This is to produce a compound represented by:

塩基としては、ジメチルホルムアミド等の溶媒中ナトリ
ウムメトキシド、ナトリウムエトキシド、カリウム−ｔ
−ブトキシド等を用いるが又は溶媒効果を兼ねてジエチ
ルアミン等を用いることが出来る。触媒としては、ニッ
ケルまたはパラジウムのトリフェニルフォスフインを普
体を０．１〜１．５当量用いることができる。さらに、
触媒は単体又は０、１〜１．０当量のハロゲン化銅（例
えば、塩化銅、臭化銅又はヨウ化銅）と共に用いること
ができる。As a base, sodium methoxide, sodium ethoxide, potassium-t in a solvent such as dimethylformamide, etc.
-Butoxide or the like can be used, but diethylamine or the like can also be used to have a solvent effect. As the catalyst, nickel or palladium triphenylphosphine can be used in an amount of usually 0.1 to 1.5 equivalents. moreover,
The catalyst can be used alone or with 0, 1 to 1.0 equivalents of copper halide (eg copper chloride, copper bromide or copper iodide).

反応温度としては、０〜１５０°Ｃが選択されるが、反
応操作の容易さから、２０〜１００°Ｃで行うのが好ま
しい。The reaction temperature is selected from 0 to 150°C, but from the viewpoint of ease of reaction operation, it is preferably carried out at 20 to 100°C.

尚、保護基としては、テトラヒドロピラニル基、アセチ
ル基等を挙げることができる。又前記式〔Ｉ［Ｉ）で表
される化合物は、−船蔵〔ｖ〕で表わされる化合物〔式
中Ｘはハロゲン原子（塩素、臭素、ヨウ素）を、Ｚはハ
ロゲン原子（塩素、臭素、ヨウ素）又は、メタンスルホ
ニル基又は、ｐ−）ルエンスルホニル基を表わす〕とイ
ミダゾールとを反応させることにより容易に得ることが
出来る。Incidentally, examples of the protecting group include a tetrahydropyranyl group and an acetyl group. Further, the compound represented by the above formula [I [I] is a compound represented by -Funezo [v] [where X is a halogen atom (chlorine, bromine, iodine), and Z is a halogen atom (chlorine, bromine, It can be easily obtained by reacting iodine) or methanesulfonyl group or p-)luenesulfonyl group] with imidazole.

〔第二工程〕[Second process]

本工程は、前記第一工程で得られる前記式ＣＩ）で表わ
される化合物を還元し、前記式（Ｖｌ）で表わされる化
合物を製造するものである。In this step, the compound represented by the formula (CI) obtained in the first step is reduced to produce the compound represented by the formula (Vl).

還元反応は、Ｐｄ系触媒〔例えばＰｄ／ＢａＣ０：＋　
。The reduction reaction is carried out using a Pd-based catalyst [e.g. Pd/BaC0:+
.

Ｐｄ／　ＣａＣ０１，Ｐｄ／　ＣａＣ０：＋−Ｐｂ（Ｏ
へＣ）〕、ラネーニ・メチル又は漆原Ｃｏ等の触媒の存
在下常圧接触水素添加するか又は、ｎ−水素化トリブチ
ル錫のようなを機錫化合物と共に加熱またはビス（シク
ロペンタジェニル）ジカルボニルチタンと共に加熱加圧
することにより行なわれる。Pd/CaC01, Pd/CaC0:+-Pb(O
C)], hydrogenated at atmospheric pressure in the presence of a catalyst such as Raneni methyl or Urushibara Co, or heated with a tin compound such as n-tributyltin hydride or bis(cyclopentadienyl)di This is carried out by heating and pressing together with carbonyl titanium.

〔第三工程〕[Third step]

本工程は、前記第二工程で得られる前記式（Ｖｌ）で表
わされる化合物を更に脱保護し、前記式〔■〕で表わさ
れる化合物を製造するものである。In this step, the compound represented by the formula (Vl) obtained in the second step is further deprotected to produce the compound represented by the formula [■].

脱保護反応は、相当する保護基の脱保護条件（例えば、
酸処理）で反応させたのち、通常の単離操作を行ない目
的物を得ることが出来る。The deprotection reaction is carried out under the deprotection conditions of the corresponding protecting group (e.g.
After the reaction (acid treatment), the desired product can be obtained by performing usual isolation operations.

参考例 １−ブロモ−４−（１−イミダゾリルメチル）ベンゼン
の合成 イミダゾール３．４０　ｇ　（５０ｍｏｆ）をアセトニ
トリル３４＋＋ｆに溶解し、４−ブロモベンジルブロマ
イド２．５０ｇ　（１０ｍｏｆ）のアセトニトリル溶液
を室温で滴下した。１２時間攪拌したのち、溶媒を減圧
留去した。残渣をクロロホルムに溶解し、水洗した後無
水硫酸ナトリウムで乾燥し、溶媒を減圧留去して標記化
合物２．２５ｇ（収率９５％）を得た。Reference Example 1 - Synthesis of bromo-4-(1-imidazolylmethyl)benzene 3.40 g (50 mof) of imidazole was dissolved in 34++f of acetonitrile, and a solution of 2.50 g (10 mof) of 4-bromobenzyl bromide in acetonitrile was added dropwise at room temperature. did. After stirring for 12 hours, the solvent was distilled off under reduced pressure. The residue was dissolved in chloroform, washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 2.25 g (yield: 95%) of the title compound.

実施例１ ３−　（４−（１−イミダゾリルメチル）フェニルシー
２−プロピン−１−オールの合成 １−ブロモ−４−（１−イミダゾリルメチル）ベンゼン
１．１９　ｇ　（５ｍ　ｍｏｆ）及びビストリフェニル
フォスフインパラジウムジクロライＦ０．０３５ｇ　（
０，０５ｍ　１１１ｏｆ　）のジエチルアミン溶液に、
窒素雰囲気中ヨウ化銅０．００４８ｇ　（０，０２５ｍ
　ｍｏｂ　）を加えた。プロパルギルアルコール０．２
８ｇ（５ｍｍｏｆ）を室温で滴下し、更に６時間攪拌し
た。ジエチルアミンを減圧留去し、残渣に水を加えた。Example 1 Synthesis of 3-(4-(1-imidazolylmethyl)phenylcy-2-propyn-1-ol) 1-bromo-4-(1-imidazolylmethyl)benzene 1.19 g (5 m mof) and bistriphenylphos Fin Palladium Dichlorite F0.035g (
0.05m 111of) of diethylamine solution,
Copper iodide 0.0048g (0,025m) in nitrogen atmosphere
mob) was added. Propargyl alcohol 0.2
8 g (5 mmof) was added dropwise at room temperature and further stirred for 6 hours. Diethylamine was distilled off under reduced pressure, and water was added to the residue.

クロロホルムで抽出し、水洗した後無水硫酸ナトリウム
で乾燥し、溶媒を減圧留去した。カラムクロマトグラフ
ィーに供し、標記化合物０．７５　ｇ（収率７０％）を
得た。The extract was extracted with chloroform, washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. It was subjected to column chromatography to obtain 0.75 g (yield 70%) of the title compound.

Ｎ　Ｍ　Ｒ（ＣＤ　Ｃｅ　３）δ：　２．４７（ＩＲ，
ｓ）、４．５６（２ｔｌ、ｓ）。NMR(CDCe3)δ: 2.47(IR,
s), 4.56 (2tl, s).

５．１３（２Ｈ，ｓ）、６．９２（ＬＨ，ｓ）、７．０
８（ｌｔｌ、ｓ）、７．０９（２Ｈ，ｄ、Ｊ＝８Ｈｚ）
、７．４２（２ｔｌ、ｄ、Ｊ＝８１１ｚ）、７．６５（
ＩＨ。5.13 (2H, s), 6.92 (LH, s), 7.0
8 (ltl, s), 7.09 (2H, d, J=8Hz)
, 7.42 (2tl, d, J=811z), 7.65 (
IH.

Ｓ） 実施例２ （Ｅ）−１−Ｃ４−（１−イミダゾリルメチル）フェニ
ルシー２−プロペン−１−オール 、３−　［１−（１−イミダゾリルメチル）フェニル］
−２−プロピンー１−オール０．７５　ｇ　（３，５ｍ
ｍｏｆ）をメタノール中、ｎ−水酸化トリブチル錫１．
０２　ｇ　（３，５ｍ　ｍｏｆ）と共に１５時間加熱還
流した。カラムクロマトグラフィーに供し、標記化合物
０．６１ｇ（収率８１％）を得た。S) Example 2 (E)-1-C4-(1-imidazolylmethyl)phenylcy2-propen-1-ol, 3-[1-(1-imidazolylmethyl)phenyl]
-2-propyn-1-ol 0.75 g (3.5 m
mof) in methanol, n-tributyltin hydroxide 1.
The mixture was heated to reflux for 15 hours with 0.2 g (3.5 mmof). It was subjected to column chromatography to obtain 0.61 g (yield: 81%) of the title compound.

ＮＭＲ（ＣＤ　Ｃｌ１３）δ：　２．２１（１８，ｓ）
、４．３３（２）１．ｄ、Ｊ＝６Ｈｚ）、５．０９（２
Ｈ，ｓ）、６．３７（１８，ｄｔ、Ｊ＝１５Ｈｚ、６）
１ｚ）。NMR (CD Cl13) δ: 2.21 (18, s)
, 4.33(2)1. d, J=6Hz), 5.09(2
H, s), 6.37 (18, dt, J=15Hz, 6)
1z).

６．６１（１）１．ｄ、Ｊ＝１５Ｈ２）、６．８９（１
肥ｓ）、７．０８（ＩＨ，ｓ）。6.61(1)1. d, J=15H2), 6.89(1
IH, s), 7.08 (IH, s).

７．０９（２Ｈ，ｄ、Ｊ＝９Ｈｚ）、７．３６（２Ｈ，
ｄ、Ｊ＝９）１ｚ）、７．５３（１８，ｓ） 質量分析　Ｃｌ３８１４Ｎ２０ 理論値　２１４．１１０６７ 実測値　２１４．１１１８７ 実施例３ （Ｚ）−３−Ｃ４−（１−イミダゾリルメチル）フェニ
ル〕−２−プロペンー１−オール ３−　（４−（１−イミダゾリルメチル）フェニル〕＝
２−プロピンー１−オール０．４２　ｇ　（２ａ＋　ｍ
ｏｆｆｉ）をメタノールに溶解し、触媒として５％パラ
ジウム−硫酸バリウム４■およびキノリン４■を加え、
室温で１２時間接触水素添加反応を行った。メタノール
を減圧留去したのち、カラムクロマトグラフィーに供し
、標記化合物０．３７ｇ（収率８７％）を得た。7.09 (2H, d, J=9Hz), 7.36 (2H,
d, J=9)1z), 7.53 (18, s) Mass spectrometry Cl3814N20 Theoretical value 214.11067 Actual value 214.11187 Example 3 (Z)-3-C4-(1-imidazolylmethyl)phenyl]- 2-propen-1-ol 3- (4-(1-imidazolylmethyl)phenyl)=
2-propyn-1-ol 0.42 g (2a+ m
offi) was dissolved in methanol, 5% palladium-barium sulfate (4) and quinoline (4) were added as catalysts,
Catalytic hydrogenation reaction was carried out at room temperature for 12 hours. After methanol was distilled off under reduced pressure, the residue was subjected to column chromatography to obtain 0.37 g (yield: 87%) of the title compound.

Ｎ　Ｍ　Ｒ（ＣＤ　Ｃ１ｓ）δ：　　１．９３（１１１
，ｓＬ４．４２（２１１，ｄ、Ｊ・７Ｈｚ）、５．１４
（２８，ｓ）、５．９２（ＬＨ，ｄｔ、Ｊ＝１２Ｈｚ、
７Ｈｚ）。NMR (CD C1s) δ: 1.93 (111
, sL4.42 (211, d, J・7Hz), 5.14
(28,s), 5.92(LH,dt, J=12Hz,
7Hz).

６．５５（１Ｂ、ｄ、Ｊ＝１２Ｈｚ）、６．９３（１Ｂ
、ｓ）、７．１３（ＩＨ，ｓ）。6.55 (1B, d, J = 12Hz), 6.93 (1B
, s), 7.13 (IH, s).

７．１４　（２）１．　ｄ、　Ｊ＝９Ｈ２）　、　７．
２１　（２Ｈ，ｄ、　Ｊ＝９Ｈｚ）　、　７．６６（Ｉ
Ｈ，ｓ） 質量分析　Ｃ＋３Ｈ＋ＪｚＯ 理論値　２１４．１１０６７ 実測値　２１４．１１１８７ 〔発明の効果〕 本発明の方法により得られる化合物は、カルシウム拮抗
作用に基づく血管拡張作用と、血小板凝集作用を併せ持
つ有用な化合物に誘導することができる。又本発明は、
本発明化合物を得るための反応操作が簡便であり、工業
的大量生産に有用な方法である。7.14 (2)1. d, J=9H2), 7.
21 (2H, d, J=9Hz), 7.66 (I
H, s) Mass spectrometry C+3H+JzO Theoretical value 214.11067 Actual value 214.11187 [Effects of the invention] The compound obtained by the method of the present invention is a useful compound that has both vasodilatory action based on calcium antagonism and platelet aggregation action. can be induced to Moreover, the present invention
The reaction operation for obtaining the compound of the present invention is simple, and the method is useful for industrial mass production.

特許出願人　冨士レビオ株式会社Patent applicant: Fujirebio Co., Ltd.

Claims (2)

【特許請求の範囲】[Claims] （１）一般式 ▲数式、化学式、表等があります▼ で表される化合物（式中Ｒは水素原子又は水酸基の補護
基である。）を還元し、更に脱保護することからなる構
造式 ▲数式、化学式、表等があります▼ で表される３−〔４−（１−イミダゾリルメチル）フェ
ニル〕−２−プロペン−１−オールの製造方法(1) Structural formula consisting of reducing and further deprotecting a compound represented by the general formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R is a hydrogen atom or a protecting group for a hydroxyl group.) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ Method for producing 3-[4-(1-imidazolylmethyl)phenyl]-2-propen-1-ol （２）一般式 ▲数式、化学式、表等があります▼ で表される化合物（式中Ｘはハロゲン原子である。）と
一般式 ▲数式、化学式、表等があります▼ で表されるアセチレン誘導体（式中Ｙは、水素原子、ニ
ッケル原子、銅原子である。）を触媒存在下反応させ一
般式 ▲数式、化学式、表等があります▼ で表される化合物を得、ついで還元し、更に脱保護する
ことからなる構造式 ▲数式、化学式、表等があります▼ で表される３−〔４−（１−イミダゾリルメチル）フェ
ニル〕−２−プロペン−１−オールの製造方法(2) Compounds represented by the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, X is a halogen atom.) and acetylene derivatives represented by the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, Y is a hydrogen atom, a nickel atom, or a copper atom.) are reacted in the presence of a catalyst to obtain a compound represented by the general formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼, which is then reduced and further decomposed. Method for producing 3-[4-(1-imidazolylmethyl)phenyl]-2-propen-1-ol represented by the structural formula ▲Mathematical formulas, chemical formulas, tables, etc.▼
JP2148534A 1990-06-08 1990-06-08 Production of 3-(4-1-imidazolylmethyl)phenyl)-2-propene-1-ol Pending JPH0441479A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2148534A JPH0441479A (en) 1990-06-08 1990-06-08 Production of 3-(4-1-imidazolylmethyl)phenyl)-2-propene-1-ol

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP2148534A JPH0441479A (en) 1990-06-08 1990-06-08 Production of 3-(4-1-imidazolylmethyl)phenyl)-2-propene-1-ol

Publications (1)

Publication Number Publication Date
JPH0441479A true JPH0441479A (en) 1992-02-12

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ID=15454930

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JP (1) JPH0441479A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7407187B2 (en) 2003-01-17 2008-08-05 Toyota Jidosha Kabushiki Kaisha Two-wheeled vehicle and chassis braking system

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* Cited by examiner, † Cited by third party
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JPH01250375A (en) * 1987-12-18 1989-10-05 Fujirebio Inc 1,4-dihydropyridine derivative

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01250375A (en) * 1987-12-18 1989-10-05 Fujirebio Inc 1,4-dihydropyridine derivative

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7407187B2 (en) 2003-01-17 2008-08-05 Toyota Jidosha Kabushiki Kaisha Two-wheeled vehicle and chassis braking system

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