FR2972453B1 - NOVEL PROCESS FOR THE SYNTHESIS OF METHYL (1R, 2S, 5S) -6,6-DIMETHYL-3-AZABICYCLO [3.1.0] HEXANE-2-CARBOXYLATE OR ONE OF ITS SALTS - Google Patents

NOVEL PROCESS FOR THE SYNTHESIS OF METHYL (1R, 2S, 5S) -6,6-DIMETHYL-3-AZABICYCLO [3.1.0] HEXANE-2-CARBOXYLATE OR ONE OF ITS SALTS

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Publication number
FR2972453B1
FR2972453B1 FR1151928A FR1151928A FR2972453B1 FR 2972453 B1 FR2972453 B1 FR 2972453B1 FR 1151928 A FR1151928 A FR 1151928A FR 1151928 A FR1151928 A FR 1151928A FR 2972453 B1 FR2972453 B1 FR 2972453B1
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France
Prior art keywords
hexane
dimethyl
azabicyclo
give
carboxylate
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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.)
Expired - Fee Related
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FR1151928A
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French (fr)
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FR2972453A1 (en
Inventor
Thierry Berranger
Patrice Demonchaux
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Minakem SAS
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Minakem SAS
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Publication date
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Priority to FR1151928A priority Critical patent/FR2972453B1/en
Publication of FR2972453A1 publication Critical patent/FR2972453A1/en
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Publication of FR2972453B1 publication Critical patent/FR2972453B1/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Indole Compounds (AREA)

Abstract

Preparing (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-methyl carboxylate (A), comprises (a) substituting (1R,5S)-2-hydroxy-6,6-dim ethyl-bicyclo[3.1.0]hexane-3-carboxylic acid 1,1-dimethyl-propyl ester by hydroxyl compound to give pyrrolidine compound (I), (b) cyaniding (I) to give 1,1-dimethylpropyl (1R,2S,5S)-2-cyano-6,6-dimethyl-3-azab icyclo[3.1.0]hexane-3-carboxylate, and (c) deprotecting the 1,1-dimethylpropyl (1R,2S,5S)-2-cyano-6,6-dimethyl-3-azabicyclo[3.1.0 ]hexane-3-carboxylate to give (A). Preparing (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-methyl carboxylate (A), comprises (a) substituting (1R,5S)-2-hydroxy-6,6-dim ethyl-bicyclo[3.1.0]hexane-3-carboxylic acid 1,1-dimethyl-propyl ester by hydroxyl compound of formula (Alk-OH) to give pyrrolidine compound of formula (I), (b) cyaniding (I) to give 1,1-dimethylpropyl (1R,2S,5S)-2-cyano-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-3-carboxyl ate, and (c) alcoholysis and deprotecting the 1,1-dimethylpropyl (1R,2S,5S)-2-cyano-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-3-carboxyl ate to give (A).Alk = 1-6C alkyl. Independent claims are included for: (1) (1R,5S)-6,6-dimethyl-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester compound of formula (II); and (2) the preparation of boceprevir, comprising (A). Either R1, R2 : H; and R2 : -OH, O-Alk or -CN; or R1R2 : (C=O). [Image] [Image] - ACTIVITY : Antiinflammatory; Hepatotropic; Virucide. - MECHANISM OF ACTION : None given.
FR1151928A 2011-03-09 2011-03-09 NOVEL PROCESS FOR THE SYNTHESIS OF METHYL (1R, 2S, 5S) -6,6-DIMETHYL-3-AZABICYCLO [3.1.0] HEXANE-2-CARBOXYLATE OR ONE OF ITS SALTS Expired - Fee Related FR2972453B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR1151928A FR2972453B1 (en) 2011-03-09 2011-03-09 NOVEL PROCESS FOR THE SYNTHESIS OF METHYL (1R, 2S, 5S) -6,6-DIMETHYL-3-AZABICYCLO [3.1.0] HEXANE-2-CARBOXYLATE OR ONE OF ITS SALTS

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR1151928A FR2972453B1 (en) 2011-03-09 2011-03-09 NOVEL PROCESS FOR THE SYNTHESIS OF METHYL (1R, 2S, 5S) -6,6-DIMETHYL-3-AZABICYCLO [3.1.0] HEXANE-2-CARBOXYLATE OR ONE OF ITS SALTS

Publications (2)

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FR2972453A1 FR2972453A1 (en) 2012-09-14
FR2972453B1 true FR2972453B1 (en) 2013-11-29

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Families Citing this family (7)

* Cited by examiner, † Cited by third party
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CN103601652A (en) * 2013-12-09 2014-02-26 上海现代制药股份有限公司 Preparation method of milnacipran hydrochloride
CN114249724B (en) * 2020-09-25 2023-05-26 鲁南制药集团股份有限公司 Preparation method of zolpidem intermediate
CN117440957A (en) * 2021-06-11 2024-01-23 帝斯曼知识产权资产管理有限公司 Process for the production of biotin intermediates
CN114456101A (en) * 2021-12-23 2022-05-10 上海璨谊生物科技有限公司 Synthesis method of key intermediate for synthesizing PF-07321332
CN114605308B (en) * 2022-03-18 2023-12-19 阜新孚隆宝医药科技有限公司 Preparation method of azabicyclo medicine intermediate of Pa Luo Weide and intermediate
CN114605310B (en) * 2022-04-09 2024-05-07 都创(上海)医药科技股份有限公司 Synthesis method of aza five-membered ring and three-membered ring carboxylic ester derivative and salt thereof
CN117384082A (en) * 2022-07-20 2024-01-12 杭州国瑞生物科技有限公司 Synthesis method of 6, 6-dimethyl-3-azabicyclo [3.1.0] hexane

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US7309717B2 (en) * 2003-06-17 2007-12-18 Schering Corporation Process and intermediates for the preparation of (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3,1,0]hexane-2-carboxylates or salts thereof
CN101421238B (en) * 2006-04-17 2013-01-09 住友化学株式会社 Method for producing polycyclic proline derivative or acid addition salt thereof

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