FR2208902A1 - 14-Hydroxy dihydronormorphinone prepn. - from 1-halo-nor codeinone, by oxidn., catalytic redn. and hydrolysis - Google Patents

14-Hydroxy dihydronormorphinone prepn. - from 1-halo-nor codeinone, by oxidn., catalytic redn. and hydrolysis

Info

Publication number
FR2208902A1
FR2208902A1 FR7321916A FR7321916A FR2208902A1 FR 2208902 A1 FR2208902 A1 FR 2208902A1 FR 7321916 A FR7321916 A FR 7321916A FR 7321916 A FR7321916 A FR 7321916A FR 2208902 A1 FR2208902 A1 FR 2208902A1
Authority
FR
France
Prior art keywords
dihydronormorphinone
codeinone
oxidn
prepn
halo
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Withdrawn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
FR7321916A
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 FR2208902A1 publication Critical patent/FR2208902A1/en
Withdrawn legal-status Critical Current

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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

14-Hydroxydihydronormorphinone is prepd. (a) by oxdn. pref. using Na dichromate of a cpd. of formula (I): (where X is Cl or Br, Y is -CHO, -COOCH3 or -COOC2H5) to give cpd. of formula (II): (b) cpd. (II) is catalytically reduced to cpd. of formula (III): and (c) cpd. (III) is hydrolysed.
FR7321916A 1972-06-15 1973-06-15 14-Hydroxy dihydronormorphinone prepn. - from 1-halo-nor codeinone, by oxidn., catalytic redn. and hydrolysis Withdrawn FR2208902A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US26308472A 1972-06-15 1972-06-15

Publications (1)

Publication Number Publication Date
FR2208902A1 true FR2208902A1 (en) 1974-06-28

Family

ID=23000315

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7321916A Withdrawn FR2208902A1 (en) 1972-06-15 1973-06-15 14-Hydroxy dihydronormorphinone prepn. - from 1-halo-nor codeinone, by oxidn., catalytic redn. and hydrolysis

Country Status (1)

Country Link
FR (1) FR2208902A1 (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4141897A (en) * 1976-12-20 1979-02-27 Research Corporation N-dealkylation of N-alkyl-14-hydroxymorphinans and derivatives thereof
FR2515184A1 (en) * 1981-08-17 1983-04-29 Univ Florida State SYNTHESES OF CODEINE DERIVATIVES AND OTHER 3-O-ALKYLMORPHINS AND INTERMEDIATE COMPOUNDS USED THEREOF
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
WO1991005768A1 (en) * 1989-10-16 1991-05-02 The United States Of America, Represented By The Secretary, United States Department Of Commerce Total synthesis of northebaine, normorphine, noroxymorphone enantiomers and derivatives via n-nor intermediates
US5668285A (en) * 1986-10-31 1997-09-16 The United States Of America As Represented By The Department Of Health And Human Services Total synthesis of northebaine, normophine, noroxymorphone enantiomers and derivatives via N-Nor intermediates

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4141897A (en) * 1976-12-20 1979-02-27 Research Corporation N-dealkylation of N-alkyl-14-hydroxymorphinans and derivatives thereof
FR2515184A1 (en) * 1981-08-17 1983-04-29 Univ Florida State SYNTHESES OF CODEINE DERIVATIVES AND OTHER 3-O-ALKYLMORPHINS AND INTERMEDIATE COMPOUNDS USED THEREOF
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
US5668285A (en) * 1986-10-31 1997-09-16 The United States Of America As Represented By The Department Of Health And Human Services Total synthesis of northebaine, normophine, noroxymorphone enantiomers and derivatives via N-Nor intermediates
WO1991005768A1 (en) * 1989-10-16 1991-05-02 The United States Of America, Represented By The Secretary, United States Department Of Commerce Total synthesis of northebaine, normorphine, noroxymorphone enantiomers and derivatives via n-nor intermediates

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Legal Events

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ST Notification of lapse