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WO2006013965A1 - Procédé de fabrication de sulfone tricyclique - Google Patents

Procédé de fabrication de sulfone tricyclique Download PDF

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Publication number
WO2006013965A1
WO2006013965A1 PCT/JP2005/014409 JP2005014409W WO2006013965A1 WO 2006013965 A1 WO2006013965 A1 WO 2006013965A1 JP 2005014409 W JP2005014409 W JP 2005014409W WO 2006013965 A1 WO2006013965 A1 WO 2006013965A1
Authority
WO
WIPO (PCT)
Prior art keywords
tricyclic
substituted
producing
compound
formula
Prior art date
Application number
PCT/JP2005/014409
Other languages
English (en)
Japanese (ja)
Inventor
Eiichiro Imai
Yukiteru Mimura
Noriko Koizumi
Sachiko Kato
Masahiko Kinugawa
Toru Sugaya
Original Assignee
Kyowa Hakko Kogyo Co., Ltd.
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 Kyowa Hakko Kogyo Co., Ltd. filed Critical Kyowa Hakko Kogyo Co., Ltd.
Priority to JP2006531588A priority Critical patent/JPWO2006013965A1/ja
Publication of WO2006013965A1 publication Critical patent/WO2006013965A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

Definitions

  • the present invention relates to a method for producing a tricyclic sulfone useful as a pharmaceutical product or a synthetic intermediate thereof.
  • Patent Document 1 Pamphlet of International Publication No. 98/46587
  • Patent Document 2 JP 2002-53580 A
  • An object of the present invention is to provide a method for producing a tricyclic sulfone that is safer and has a higher yield than conventional methods and is suitable for mass synthesis.
  • the present invention relates to the following (1) to (5).
  • X is a hydrogen atom, halogen, substituted or unsubstituted alkyl, mono (substituted or unsubstituted alkyl) aminocarbol, di (substituted or unsubstituted alkyl) aminocarbo]
  • the present invention provides a method for producing a tricyclic sulfone that is safer and has a higher yield than conventional methods and is suitable for mass synthesis.
  • Halogen represents each atom of fluorine, chlorine, bromine and iodine.
  • alkyl moiety of alkyl, mono (alkyl) aminocarbol, di (alkyl) aminocarbole and alkanoylamino examples include, for example, linear, branched, cyclic, or a combination thereof having 1 to 10 carbon atoms.
  • Alkyl is mentioned. Note that the two alkyl moieties in the di (alkyl) aminocarboxyl may be the same or different! /, May! /.
  • linear or branched alkyl examples include methyl, ethyl, n-propyl, isopropinole, n-butyl, isobutyl, sec-butynole, tert-butyl, n-pentyl, neopentyl, n- Hexyl, n-heptyl, n-octyl, n-nor, n-decyl and the like can be mentioned.
  • cyclic alkyl examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecyl, noradamantyl, adamantyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl, bicyclo [ 3.3.0] octyl, bicyclo [3.3.1] nor and the like.
  • alkyl having a combination force of linear or branched and cyclic examples include cyclopropylmethyl, cyclopentylmethyl, cyclooctylethyl and the like.
  • the substituents in substituted alkyl, mono (substituted alkyl) aminocarbol, di (substituted alkyl) aminocarbol and substituted alkanoylamino are the same or different and can be substituted from the number of substitutions 1, preferably the number of substitutions. 1 to 4, for example, halogen, amino-containing hydroxy, alkoxy, aryl, heterocyclic group and the like can be mentioned.
  • substituted alkyl mono (substituted alkyl) aminocarbol, di (substituted alkyl) aminocarbol and substituted alkanoylamino, the halogen is as defined above, and the alkyl part of alkoxy is as defined above. It is synonymous with alkyl, and examples of aryl include fur and naphthyl, and examples of heterocyclic groups include aromatic heterocyclic groups and alicyclic heterocyclic groups.
  • Examples of the aromatic heterocyclic group include pyridyl, furyl, chenyl, quinolyl, imidazolyl, benzoimidazolyl, thiazolyl, oxazolyl and the like, and examples of the alicyclic heterocyclic group include tetrahydrofuryl, tetrahydrophenylenole, and chromyl. , Pyrrolidyl, piperazil, piperidyl, pipecolinyl, monorephoryl, thiomorpholinyl and the like.
  • Compound (II) can be produced, for example, by the following method.
  • Compound (I) is added to 1 to 100 equivalents, preferably 1 to 5 equivalents of oxone (registered trademark) with compound (I) in a solvent, preferably a hydrous solvent, more preferably a hydrous ⁇ , ⁇ - Dimethylformamide (DMF), hydrous acetonitrile, hydrous methanol, hydrous acetone or hydrous 1,4-dioxane, more preferably hydrous DMF or hydrous acetonitrile, from -78 ° C
  • Compound (II) can be obtained by reacting at a temperature between the boiling points of the solvents, preferably at a temperature between 0 and 60 ° C., for 5 minutes to 24 hours, preferably 2 to 10 hours.
  • Compound (I) can be obtained by the method described in W098 / 46587, JP-A-2002-53580 or the like, or a method analogous thereto.
  • W098 / 46587 and JP-A-2002-53580 describe an oxidation reaction from compound 2 to compound 1 using methacrobenzoic perbenzoic acid. In this case, the yield of compound 1 is! All were 65%.
  • the reaction mixture was stirred at the same temperature for 2 hours, then washed twice with 2 mol / L aqueous sodium hydroxide solution (60 mL, 80 mL) and once with 10% aqueous sodium sulfate solution (80 mL), and the solvent was distilled under reduced pressure. After leaving, the obtained residue was dissolved in DMF (45 mL) and water (15 mL) at 35 ° C, and Oxon (registered trademark) (Mitsubishi Gas Chemical) (31.7 g, 51.6 mmol) was added at the same temperature. It was.
  • Oxon registered trademark
  • acid conversion from tricyclic sulfide to tricyclic sulfone can be performed in high yield.
  • Oxone registered trademark
  • Oxone is a safer oxidant than oxidants such as metachloroperbenzoic acid, and is considered to be particularly suitable for use on a large scale!
  • Example 1 Compound 1 (10.0 g, 23.8 mmol) obtained in Example 1 was dissolved in ethanol (225 mL) by heating to obtain water (225 mL). After cooling, crystallization was performed for 3 hours under ice cooling to obtain Compound 1 (9.7 g, yield 97%) with a purity of 99.9% or more (high performance liquid chromatography analysis) as a pale yellowish white solid. .
  • a tricyclic system that is safer and has higher yield than conventional methods and is suitable for mass synthesis.
  • a process for the production of sulfones is provided.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L’invention porte sur un procédé de fabrication de sulfone tricyclique représenté par la formule (II) [où X représente de l’hydrogène, un halogène, un alkyle (non)substitué, un aminocarbonyle mono((non)substitué alkyle), un aminocarbonyle di((non)substitué alkyle) ou bien un alkanoylaminé (non)substitué], caractérisé par l’oxydation d’un sulfure tricyclique représenté par la formule (I) (où X a le même sens que ci-dessus) avec un sel composite de monopersulfate d’hydrogène potassium (2KHSO5·KHSO4·K2SO4). (I) (II)
PCT/JP2005/014409 2004-08-06 2005-08-05 Procédé de fabrication de sulfone tricyclique WO2006013965A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2006531588A JPWO2006013965A1 (ja) 2004-08-06 2005-08-05 三環系スルホンの製造法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2004-231392 2004-08-06
JP2004231392 2004-08-06

Publications (1)

Publication Number Publication Date
WO2006013965A1 true WO2006013965A1 (fr) 2006-02-09

Family

ID=35787243

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2005/014409 WO2006013965A1 (fr) 2004-08-06 2005-08-05 Procédé de fabrication de sulfone tricyclique

Country Status (2)

Country Link
JP (1) JPWO2006013965A1 (fr)
WO (1) WO2006013965A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998046587A1 (fr) * 1997-04-15 1998-10-22 Kyowa Hakko Kogyo Co., Ltd. Composes tricycliques
JP2002053580A (ja) * 2000-08-09 2002-02-19 Kyowa Hakko Kogyo Co Ltd 三環系化合物の製造法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998046587A1 (fr) * 1997-04-15 1998-10-22 Kyowa Hakko Kogyo Co., Ltd. Composes tricycliques
JP2002053580A (ja) * 2000-08-09 2002-02-19 Kyowa Hakko Kogyo Co Ltd 三環系化合物の製造法

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
POSS K.M. ET AL: "Diastereoselective Oxidation of Sulfides to Sulfoxides. Synthesis of Novel C-6 Sulfoxy Tetrahydromevinic Acids", TETRAHEDRON LETTERS, vol. 35, no. 21, 1994, pages 3461 - 3464, XP001022390 *
TROST B.M. ET AL: "Chemoselective Oxidation of Sulfides to Sulfones with Potassium Hydrogen Persufate", TETRAHEDRON LETTERS, vol. 22, no. 14, 1981, pages 1287 - 1290, XP009018367 *

Also Published As

Publication number Publication date
JPWO2006013965A1 (ja) 2008-05-01

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