NZ212193A - Dealkylation of 14-hydroxy-morphinan alkaloids; intermediates therefor - Google Patents

Dealkylation of 14-hydroxy-morphinan alkaloids; intermediates therefor

Info

Publication number
NZ212193A
NZ212193A NZ212193A NZ21219385A NZ212193A NZ 212193 A NZ212193 A NZ 212193A NZ 212193 A NZ212193 A NZ 212193A NZ 21219385 A NZ21219385 A NZ 21219385A NZ 212193 A NZ212193 A NZ 212193A
Authority
NZ
New Zealand
Prior art keywords
dealkylation
hydroxy
formula
intermediates therefor
see diagramm
Prior art date
Application number
NZ212193A
Inventor
C Hoff
C Vergely
Original Assignee
Sanofi Sa
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 Sanofi Sa filed Critical Sanofi Sa
Publication of NZ212193A publication Critical patent/NZ212193A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
    • C07D489/06—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with a hetero atom directly attached in position 14
    • C07D489/08—Oxygen atom
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Saccharide Compounds (AREA)
  • Steroid Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)

Abstract

1. A process for the dealkylation of 14-hydroxymorphinan alkaloids, characterized in that it consists in : 1) reacting the 14-hydroxy derivative of the formula : see diagramm : EP0164290,P5,F6 in which R' is CH3 or COCH3 , with excess ethyl chloroformate, in the presence of potassium carbonate and in a solvent, 2) subjecting the resulting carbamate of the formula : see diagramm : EP0164290,P5,F2 in which R' is CH3 or COCH3 , to hydrolysis in a strong acid medium to give the corresponding dealkylated derivative of the formula : see diagramm : EP0164290,P5,F3 in which R is CH3 or hydrogen.
NZ212193A 1984-05-25 1985-05-24 Dealkylation of 14-hydroxy-morphinan alkaloids; intermediates therefor NZ212193A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR8408273A FR2564838B1 (en) 1984-05-25 1984-05-25 PROCESS FOR DEALKYLATION OF ALKALOIDS AND INTERMEDIATES

Publications (1)

Publication Number Publication Date
NZ212193A true NZ212193A (en) 1988-10-28

Family

ID=9304425

Family Applications (1)

Application Number Title Priority Date Filing Date
NZ212193A NZ212193A (en) 1984-05-25 1985-05-24 Dealkylation of 14-hydroxy-morphinan alkaloids; intermediates therefor

Country Status (12)

Country Link
EP (1) EP0164290B1 (en)
JP (1) JPS60258183A (en)
AT (1) ATE46163T1 (en)
AU (1) AU577379B2 (en)
CA (1) CA1244825A (en)
DE (1) DE3572819D1 (en)
DK (1) DK160048C (en)
ES (1) ES543338A0 (en)
FR (1) FR2564838B1 (en)
NO (1) NO164981C (en)
NZ (1) NZ212193A (en)
PT (1) PT80519B (en)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4795813A (en) * 1981-08-17 1989-01-03 The Florida Board Of Regents On Behalf Of The Florida State University Synthesis of derivatives of codeine and other 3-O-alkylmorphines
US6067749A (en) 1996-07-11 2000-05-30 Tasmanian Alkaloids Pty. Ltd. Papaver somniferum strain with high concentration of thebaine and oripavine
GB2438401A (en) * 2006-05-25 2007-11-28 Alpharma Aps Preparation of morphinan derivatives comprising N-demethylation, reductive amination and O-demethylation steps
GB2471802B (en) * 2006-05-25 2011-02-16 Alpharma Chemical process
GB2444052A (en) * 2006-05-25 2008-05-28 Alpharma Aps Processes of preparing morphinan derivatives such as naltrexone and naloxone comprising O- and N-demethylation and reductive alkylation steps
US8962841B2 (en) 2007-06-29 2015-02-24 Brock University Methods for one-pot N-demethylation/N-functionalization of morphine and tropane alkaloids
US7999104B2 (en) * 2007-06-29 2011-08-16 Brock University Methods for one-pot N-demethylation/N-acylation of morphine and tropane alkaloids
CA2709872C (en) * 2007-12-17 2016-06-14 Peter X. Wang Processes for the preparation of normorphinan salts
US9131649B2 (en) 2008-03-07 2015-09-15 Tasmanian Alkaloids Pty. Ltd Papaver somniferum strain with high concentration of thebaine
CA2720034A1 (en) * 2008-03-31 2009-10-08 Sun Pharmaceutical Industries Ltd. An improved process for the preparation of morphinane analogues
WO2011154827A2 (en) 2010-06-11 2011-12-15 Rhodes Technologies Transition metal-catalyzed processes for the preparation of n-allyl compounds and use thereof
AU2011263416B2 (en) 2010-06-11 2014-04-10 Rhodes Technologies Process for N-dealkylation of tertiary amines
WO2012151669A1 (en) * 2011-05-06 2012-11-15 Brock University Process for the preparation of morphine analogs via metal catalyzed n-demethylation/functionalization and intramolecular group transfer

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4141807A (en) * 1977-03-01 1979-02-27 Stauffer Chemical Company Photopolymerizable composition stabilized with nitrogen-containing aromatic compounds
DE2727805A1 (en) * 1977-06-21 1979-01-04 Goedecke Ag METHOD FOR PRODUCING OXYNORMORPHONE
US4390699A (en) * 1981-07-16 1983-06-28 The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services 6-Keto-morphinans belonging to the 14-hydroxy-series
US4472253A (en) * 1981-08-17 1984-09-18 The Florida Board Of Regents On Behalf Of The Florida State University Process for the preparation of an N-substituted 3-O-alkyl-14-hydroxynormorphinone derivative
DE3381560D1 (en) * 1982-09-24 1990-06-21 Poudres & Explosifs Ste Nale VINYLCARMABATE AND PRODUCTION METHOD.

Also Published As

Publication number Publication date
DK160048B (en) 1991-01-21
ES8603893A1 (en) 1986-01-01
FR2564838A1 (en) 1985-11-29
CA1244825A (en) 1988-11-15
NO852091L (en) 1985-11-26
JPS60258183A (en) 1985-12-20
AU577379B2 (en) 1988-09-22
NO164981C (en) 1990-12-05
PT80519B (en) 1988-01-22
AU4284385A (en) 1985-11-28
EP0164290A1 (en) 1985-12-11
FR2564838B1 (en) 1986-11-07
DE3572819D1 (en) 1989-10-12
PT80519A (en) 1985-06-01
ES543338A0 (en) 1986-01-01
DK160048C (en) 1991-06-17
DK227685A (en) 1985-11-26
ATE46163T1 (en) 1989-09-15
NO164981B (en) 1990-08-27
EP0164290B1 (en) 1989-09-06
DK227685D0 (en) 1985-05-22

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