GB1028407A - Improvements in or relating to morphinan derivatives and their preparation - Google Patents

Improvements in or relating to morphinan derivatives and their preparation

Info

Publication number
GB1028407A
GB1028407A GB1348463A GB1348463A GB1028407A GB 1028407 A GB1028407 A GB 1028407A GB 1348463 A GB1348463 A GB 1348463A GB 1348463 A GB1348463 A GB 1348463A GB 1028407 A GB1028407 A GB 1028407A
Authority
GB
United Kingdom
Prior art keywords
cis
methoxy
hydroxy
prepared
group
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.)
Expired
Application number
GB1348463A
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.)
Shionogi and Co Ltd
Original Assignee
Shionogi and 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 Shionogi and Co Ltd filed Critical Shionogi and Co Ltd
Publication of GB1028407A publication Critical patent/GB1028407A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/22—Bridged ring systems
    • C07D221/28—Morphinans

Abstract

Compounds of the Formula I are prepared by reacting a compound of the Formula II with an acylating agent to produce a compound of the Formula III, which is reduced with an alkali metal hydride complex in an inert solvent medium: <FORM:1028407/C2/1> <FORM:1028407/C2/2> <FORM:1028407/C2/3> where R represents an alkyl group of not more than five carbon atoms, R1 represents a hydrogen atom or an aryloxy group, R11 represents a methylene group, a carbonyl group or a ketalated carbonyl group, X represents a hydrogen atom or a hydroxyl group and X1 represents a hydrogen atom or a hydroxyl or acyloxy group. (-) - 3 - Methoxy - 6 - oxo - 14 - hydroxy - N-ethylmorphinan(cis) is prepared by deketalation of (-) - 3 - methoxy - 6,6 - ethylenedioxy - 14 - hydroxy - N - ethylmorphinan(cis). (-) - 3 - Methoxy - 6,6 - ethylenedioxy - 14 - hydroxy - N - acetylmorphinan(cis) is prepared by ketalation of the corresponding 6-keto compound. (-) - 3 - Methoxy - 6,6 - ethylenedioxy - 14 - hydroxy - N - methylmorphinan(cis) is prepared by ketalation of (-)-3-methoxy-4-phenoxy-6-keto - 14 - hydroxy - N - methylmorphinan (cis) to give (-) - 3 - methoxy - 4 - phenoxy - 6,6 - ethylenedioxy - 14 - hydroxy - N - methylmorphinan(cis) which is then treated with metallic sodium in liquid ammonia. (+)-3-Methoxy-morphinan(cis) is prepared from (+) - 3 - methoxy - 4 - phenyloxy - morphinan(cis) by treatment with sodium in liquid ammonia.
GB1348463A 1962-04-06 1963-04-04 Improvements in or relating to morphinan derivatives and their preparation Expired GB1028407A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP1406162 1962-04-06
JP1406062 1962-04-06

Publications (1)

Publication Number Publication Date
GB1028407A true GB1028407A (en) 1966-05-04

Family

ID=26349949

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1348463A Expired GB1028407A (en) 1962-04-06 1963-04-04 Improvements in or relating to morphinan derivatives and their preparation

Country Status (3)

Country Link
CH (1) CH460036A (en)
DE (1) DE1286045B (en)
GB (1) GB1028407A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2243961A1 (en) * 1971-09-08 1973-04-05 Bristol Myers Co PROCESS FOR PRODUCING ANALGETIC COMPOUNDS
US3980641A (en) * 1975-07-31 1976-09-14 Bristol-Myers Company Process for the preparation of 14-hydroxymorphinans

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2243961A1 (en) * 1971-09-08 1973-04-05 Bristol Myers Co PROCESS FOR PRODUCING ANALGETIC COMPOUNDS
US3980641A (en) * 1975-07-31 1976-09-14 Bristol-Myers Company Process for the preparation of 14-hydroxymorphinans

Also Published As

Publication number Publication date
CH460036A (en) 1968-07-31
DE1286045B (en) 1969-01-02

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