GB684367A - The resolution of 3-hydroxy-and 3-methoxy-n-methyl-morphinanes and process for the manufacture of the latter - Google Patents

The resolution of 3-hydroxy-and 3-methoxy-n-methyl-morphinanes and process for the manufacture of the latter

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Publication number
GB684367A
GB684367A GB26912/50A GB2691250A GB684367A GB 684367 A GB684367 A GB 684367A GB 26912/50 A GB26912/50 A GB 26912/50A GB 2691250 A GB2691250 A GB 2691250A GB 684367 A GB684367 A GB 684367A
Authority
GB
United Kingdom
Prior art keywords
methoxy
hydroxy
salts
methyl
resolution
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
GB26912/50A
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.)
Roche Products Ltd
Original Assignee
Roche Products 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 Roche Products Ltd filed Critical Roche Products Ltd
Publication of GB684367A publication Critical patent/GB684367A/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

Landscapes

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

Abstract

A method of preparing optically active 3-hydroxy and 3-methoxy-N-methyl morphinanes comprises converting racemic 3-hydroxy and 3-methoxy-N-methyl morphinane into their salts with an optically active acid, separating the salts into their optical antipodes by fractional crystallization and thereafter, if desired, basifying said antipodes and converting the free bases so formed into the required salts by treatment with the appropriate acid. Where the optically active 3-hydroxy compounds are obtained they may be methylated as free bases to the 3-methoxy compound and if desired converted to salts. Alternatively, the racemic 3-hydroxy compound may be methylated before resolution. D-tartaric acid is specified as a suitable optically-active acid. Phenyl - trimethyl - ammonium hydroxide may be used as methylating agent. Water is a suitable solvent in which to effect the resolution. To prepare (-)-3-methoxy-N-methyl morphinane crystallization of the D-tartaric acid salt may be used, the desired compound crystallizing out first, then methylating the product. (+)-3-methoxy-N-methyl-morphinane may be obtained by methylating the racemate followed by crystallization of the D-tartaric acid salts. In examples: (1) and (2) both these procedures are employed. Hydrobromides and hydroiodides of the 3-hydroxy-and 3-methoxy-compounds are prepared.
GB26912/50A 1949-11-09 1950-11-03 The resolution of 3-hydroxy-and 3-methoxy-n-methyl-morphinanes and process for the manufacture of the latter Expired GB684367A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH684367X 1949-11-09

Publications (1)

Publication Number Publication Date
GB684367A true GB684367A (en) 1952-12-17

Family

ID=4528734

Family Applications (1)

Application Number Title Priority Date Filing Date
GB26912/50A Expired GB684367A (en) 1949-11-09 1950-11-03 The resolution of 3-hydroxy-and 3-methoxy-n-methyl-morphinanes and process for the manufacture of the latter

Country Status (1)

Country Link
GB (1) GB684367A (en)

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