FR2189403A1 - Norcodeine prepn - by reduction of 1-halo-norcodeinones, novel intermedi-ates for narcotic antagonists - Google Patents

Norcodeine prepn - by reduction of 1-halo-norcodeinones, novel intermedi-ates for narcotic antagonists

Info

Publication number
FR2189403A1
FR2189403A1 FR7321915A FR7321915A FR2189403A1 FR 2189403 A1 FR2189403 A1 FR 2189403A1 FR 7321915 A FR7321915 A FR 7321915A FR 7321915 A FR7321915 A FR 7321915A FR 2189403 A1 FR2189403 A1 FR 2189403A1
Authority
FR
France
Prior art keywords
prepn
norcodeinones
norcodeine
halo
intermedi
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.)
Withdrawn
Application number
FR7321915A
Other languages
French (fr)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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 Merck and Co Inc filed Critical Merck and Co Inc
Publication of FR2189403A1 publication Critical patent/FR2189403A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D489/00Heterocyclic 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:
    • C07D489/02Heterocyclic 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 oxygen atoms attached in positions 3 and 6, e.g. morphine, morphinone

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Prepn. of norcodeins by reaction of 1-halo-norcodeinones of formula: where X is Cl or Br; and Y is CHO, -CO2Me or -CO2Et with a suitable reagent to give a cpd. of formula: which in turn is reduced to norcodeins (III): Cpds. are new. Removal of the protecting gp. Y requires mild conditions to avoid possible rearrangement of the mol. When Y = -CHO this is performed with H2O2, or aq. or alcoholic HCl or HBr. When Y is CO2Me or CO2Et alkaline hydrolysis in an inert atmos. is prefd. Norcodeine is an inter. in the prepn. of narcotic antagonists such as nalorphine or normorphine.
FR7321915A 1972-06-15 1973-06-15 Norcodeine prepn - by reduction of 1-halo-norcodeinones, novel intermedi-ates for narcotic antagonists Withdrawn FR2189403A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US26308372A 1972-06-15 1972-06-15

Publications (1)

Publication Number Publication Date
FR2189403A1 true FR2189403A1 (en) 1974-01-25

Family

ID=23000311

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7321915A Withdrawn FR2189403A1 (en) 1972-06-15 1973-06-15 Norcodeine prepn - by reduction of 1-halo-norcodeinones, novel intermedi-ates for narcotic antagonists

Country Status (1)

Country Link
FR (1) FR2189403A1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009078987A1 (en) * 2007-12-17 2009-06-25 Mallinckrodt Inc. Process and compounds for the production of (+) opiates
US8624031B2 (en) 2011-09-08 2014-01-07 Mallinckrodt Llc Production of alkaloids without the isolation of intermediates

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009078987A1 (en) * 2007-12-17 2009-06-25 Mallinckrodt Inc. Process and compounds for the production of (+) opiates
US8252808B2 (en) 2007-12-17 2012-08-28 Mallinckrodt Llc Process and compounds for the production of (+)opiates
US8624031B2 (en) 2011-09-08 2014-01-07 Mallinckrodt Llc Production of alkaloids without the isolation of intermediates

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Legal Events

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