WO2010079605A1 - Procédé de production de la 1-benzyl-3-aminopyrrolidine de pureté élevée - Google Patents

Procédé de production de la 1-benzyl-3-aminopyrrolidine de pureté élevée Download PDF

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Publication number
WO2010079605A1
WO2010079605A1 PCT/JP2009/050167 JP2009050167W WO2010079605A1 WO 2010079605 A1 WO2010079605 A1 WO 2010079605A1 JP 2009050167 W JP2009050167 W JP 2009050167W WO 2010079605 A1 WO2010079605 A1 WO 2010079605A1
Authority
WO
WIPO (PCT)
Prior art keywords
benzyl
aminopyrrolidine
water
tartaric acid
purity
Prior art date
Application number
PCT/JP2009/050167
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English (en)
Japanese (ja)
Inventor
年弘 藤野
龍治 小川
健一 酒井
Original Assignee
東レ・ファインケミカル株式会社
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 東レ・ファインケミカル株式会社 filed Critical 東レ・ファインケミカル株式会社
Priority to PCT/JP2009/050167 priority Critical patent/WO2010079605A1/fr
Priority to JP2010545664A priority patent/JP5397706B2/ja
Publication of WO2010079605A1 publication Critical patent/WO2010079605A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/14—Nitrogen atoms not forming part of a nitro radical

Definitions

  • the present invention relates to a method for purifying 1-benzyl-3-aminopyrrolidine having low chemical purity in which impurities are mixed.
  • a salt is formed from a mixture of (R) -1-benzyl-3-aminopyrrolidine represented by the formula (S) -1-benzyl-3-aminopyrrolidine and a mixture of L-tartaric acid and D-tartaric acid and mixed with water. And a method for producing high-purity 1-benzyl-3-aminopyrrolidine characterized by crystallization in a mixed solvent of an organic solvent and water.
  • high chemical purity 1-benzyl-3-aminopyrrolidine can be obtained in high yield from low chemical purity 1-benzyl-3-aminopyrrolidine by a simple industrially feasible method.
  • the chemical purity is low because it contains many impurities such as 4-amino-1-benzylpiperidine represented by Such impurities are difficult to remove because their properties are similar to racemic 1-benzyl-3-aminopyrrolidine, and from low chemical purity racemic 1-benzyl-3-aminopyrrolidine to high chemical purity racemic 1-benzyl.
  • impurities such as 4-amino-1-benzylpiperidine represented by Such impurities are difficult to remove because their properties are similar to racemic 1-benzyl-3-aminopyrrolidine, and from low chemical purity racemic 1-benzyl-3-aminopyrrolidine to high chemical purity racemic 1-benzyl.
  • a high purification yield cannot be achieved in the operation for removing impurities. Therefore, it was necessary to develop a purification method for obtaining high-purity racemic 1-benzyl-3-aminopyrrolidine in high yield.
  • Example 4 The same operation as in Example 2 was carried out except that the amount of methanol used was changed to 11.4 g and the amount of water used was changed to 4.1 g to obtain 6.4 g of a salt of 1-benzyl-3-aminopyrrolidine and tartaric acid. .
  • the content of 1-benzyl-3-aminopyrrolidine in the obtained salt was 46.3%, and the crystallization yield was 87%.
  • moisture content was 14.2%.
  • 1 g of the obtained salt, 1 g of water, 1 g of toluene, and 0.6 g of 48% aqueous sodium hydroxide solution were collected and shaken well. When the toluene layer was analyzed by gas chromatography, the chemical purity of 1-benzyl-3-aminopyrrolidine calculated by removing toluene was 99.8%.
  • Example 10 The same operation as in Example 5 was carried out except that methanol was changed to acetonitrile, to obtain 6.1 g of a salt of 1-benzyl-3-aminopyrrolidine and tartaric acid.
  • the content of 1-benzyl-3-aminopyrrolidine in the obtained salt was 46.7%, and the crystallization yield was 83%.
  • the water content was 13.7%.
  • 1 g of the obtained salt, 1 g of water, 1 g of toluene, and 0.6 g of 48% aqueous sodium hydroxide solution were collected and shaken well.
  • the toluene layer was analyzed by gas chromatography, the chemical purity of 1-benzyl-3-aminopyrrolidine calculated by removing toluene was 99.9%.
  • the cake was taken out and dried under vacuum to obtain 4.8 g of a racemic 1-benzyl-3-aminopyrrolidine and succinic acid salt.
  • the content of 1-benzyl-3-aminopyrrolidine in the obtained salt was 60.3%, and the crystallization yield was 86%.
  • 1 g of the obtained salt, 1 g of water, 1 g of toluene, and 0.6 g of 48% aqueous sodium hydroxide solution were collected and shaken well.
  • Comparative Example 8 The same operation as in Example 2 was performed except that methanol was not used and the amount of water used was changed to 15.5 g, to obtain 4.6 g of a salt of 1-benzyl-3-aminopyrrolidine and tartaric acid.
  • the content of 1-benzyl-3-aminopyrrolidine in the obtained salt was 46.9%, and the crystallization yield was 62%.
  • moisture content was 13.3%.
  • 1 g of the obtained salt, 1 g of water, 1 g of toluene, and 0.6 g of 48% aqueous sodium hydroxide solution were collected and shaken well.
  • the toluene layer was analyzed by gas chromatography, the chemical purity of 1-benzyl-3-aminopyrrolidine was 100.0% (note that toluene was excluded).
  • the mixture was cooled to about 3 ° C. over 30 minutes, and further stirred at 0 to 5 ° C. for 2 hours.
  • the slurry was filtered, and the cake was washed with 5 ml of 50% aqueous methanol solution.
  • the cake was taken out and vacuum-dried to obtain 3.2 g of 1-benzyl-3-aminopyrrolidine and tartaric acid salt.
  • the content of 1-benzyl-3-aminopyrrolidine in the obtained salt was 47.0%, and the crystallization yield was 44%.
  • the water content was 13.8%.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyrrole Compounds (AREA)

Abstract

La présente invention concerne un procédé de purification utilisable à l'échelle industrielle grâce auquel peut être produite la 1-benzyl-3-aminopyrrolidine avec une pureté chimique élevée et un rendement élevé. Un sel est formé à partir de l'acide tartrique et de la 1-benzyl-3-aminopyrrolidine de faible pureté chimique et contenant des impuretés. Le sel est cristallisé à partir d'un solvant mixte comprenant de l'eau et un solvant organique miscible avec l'eau afin de produire ainsi une 1-benzyl-3-aminopyrrolidine de pureté élevée.
PCT/JP2009/050167 2009-01-09 2009-01-09 Procédé de production de la 1-benzyl-3-aminopyrrolidine de pureté élevée WO2010079605A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/JP2009/050167 WO2010079605A1 (fr) 2009-01-09 2009-01-09 Procédé de production de la 1-benzyl-3-aminopyrrolidine de pureté élevée
JP2010545664A JP5397706B2 (ja) 2009-01-09 2009-01-09 高純度１−ベンジル−３−アミノピロリジンの製造方法

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/JP2009/050167 WO2010079605A1 (fr) 2009-01-09 2009-01-09 Procédé de production de la 1-benzyl-3-aminopyrrolidine de pureté élevée

Publications (1)

Publication Number Publication Date
WO2010079605A1 true WO2010079605A1 (fr) 2010-07-15

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Country Status (2)

Country Link
JP (1) JP5397706B2 (fr)
WO (1) WO2010079605A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102603592A (zh) * 2012-02-20 2012-07-25 上海应用技术学院 (r)-1-苄基-3-氨基吡咯烷和(s)-1-苄基-3-氨基吡咯烷的制备方法

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02218664A (ja) * 1989-02-17 1990-08-31 Tokyo Kasei Kogyo Kk 光学活性な１ｈ−３−アミノピロリジン化合物の製造法
JPH09124595A (ja) * 1995-10-26 1997-05-13 Toray Ind Inc 光学分割剤およびそれを用いた光学活性３−アミノピロリジン誘導体の製造法
JPH09176115A (ja) * 1995-12-28 1997-07-08 Koei Chem Co Ltd 光学活性なｎ−ベンジル−３−アミノピロリジンの製造方法
WO2003082815A1 (fr) * 2002-03-29 2003-10-09 Kaneka Corporation Procede d'amelioration de la purete optique de 1-benzyl-3- aminopyrrolidine et sel utilise dans ce procede
JP2007297306A (ja) * 2006-04-28 2007-11-15 Kaneka Corp 光学活性３−（１−ピロリジニル）ピロリジンの製造法
WO2008013130A1 (fr) * 2006-07-28 2008-01-31 Kaneka Corporation Méthode de production d'un composé 3-amino-azoté optiquement actif
JP2008044931A (ja) * 2006-07-14 2008-02-28 Pfizer Prod Inc （７Ｓ）−７−［（５−フルオロ−２−メチル−ベンジル）オキシ］−２−［（２Ｒ）−２−メチルピペラジン−１−イル］−６，７−ジヒドロ−５Ｈ−シクロペンタ［ｂ］ピリジンの酒石酸塩

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02218664A (ja) * 1989-02-17 1990-08-31 Tokyo Kasei Kogyo Kk 光学活性な１ｈ−３−アミノピロリジン化合物の製造法
JPH09124595A (ja) * 1995-10-26 1997-05-13 Toray Ind Inc 光学分割剤およびそれを用いた光学活性３−アミノピロリジン誘導体の製造法
JPH09176115A (ja) * 1995-12-28 1997-07-08 Koei Chem Co Ltd 光学活性なｎ−ベンジル−３−アミノピロリジンの製造方法
WO2003082815A1 (fr) * 2002-03-29 2003-10-09 Kaneka Corporation Procede d'amelioration de la purete optique de 1-benzyl-3- aminopyrrolidine et sel utilise dans ce procede
JP2007297306A (ja) * 2006-04-28 2007-11-15 Kaneka Corp 光学活性３−（１−ピロリジニル）ピロリジンの製造法
JP2008044931A (ja) * 2006-07-14 2008-02-28 Pfizer Prod Inc （７Ｓ）−７−［（５−フルオロ−２−メチル−ベンジル）オキシ］−２−［（２Ｒ）−２−メチルピペラジン−１−イル］−６，７−ジヒドロ−５Ｈ−シクロペンタ［ｂ］ピリジンの酒石酸塩
WO2008013130A1 (fr) * 2006-07-28 2008-01-31 Kaneka Corporation Méthode de production d'un composé 3-amino-azoté optiquement actif

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
AKIRA OGATA: "Kagaku Jikken Sosaho Jokan", 1963, NANKODO CO., LTD., pages: 381 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102603592A (zh) * 2012-02-20 2012-07-25 上海应用技术学院 (r)-1-苄基-3-氨基吡咯烷和(s)-1-苄基-3-氨基吡咯烷的制备方法

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JPWO2010079605A1 (ja) 2012-06-21
JP5397706B2 (ja) 2014-01-22

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