66254-53-3

Basic information

• Product Name: C₂₂H₃₁NO₂
• CAS NO: 66254-53-3
• Molecular Weight: 341.494
• Mol File: 66254-53-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: C₂₂H₃₁NO₂(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₂H₃₁NO₂(66254-53-3)
• EPA Substance Registry System: C₂₂H₃₁NO₂(66254-53-3)

Safety Data

• Hazardous Substances Data: 66254-53-3(Hazardous Substances Data)

Relevant articles and documents

Oxilorphan and butorphanol. Potent narcotic antagonists and nonaddicting analgesics in the 3,14 dihydroxymorphinan series. Part V

A series of 3,14 dihydroxymorphinans 8 was synthesized via a method of (a) acylation of 3 methoxy Δ84 morphinan 4a (b) stereospecific epoxidation of the resultant amides to β epoxides 5 (c) simultaneous reduction of amide and epoxide functions and (d) demethylation of the resultant 3 methoxy 14 hydroxymorphinans 7. Alternatively deblocking of the amine function in 5b by hydrolysis followed by reduction of the resultant amino epoxide 5e afforded 14 hydroxy 3 methoxymorphinan 7e, which is readily alkylated and demethylated to give various 8. On a basis of interesting pharmacological profiles compounds l 8c (oxilorphan) and l 8d (butorphanol) were selected for clinical studies.

A stereoselective total synthesis of 14-hydroxymorphinans, Grewe approach

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Process for the preparation of 14-hydroxymorphinans

N-substituted-14-hydroxy-3-substituted-morphinan derivatives have been found to possess potent narcotic agonist or antagonist activity. In particular, the compound 3,14-dihydroxy-N-cyclopropylmethylmorphinan has been found to possess potent agonist-antagonist activity. A new and more efficient total synthesis for the preparation of these compounds is described herein, which improvement comprises using a Schiff base of 4a-(2-aminoethyl)-1,2,3,4,4a,9-hexahydro-6-methoxyphenanthrene to produce 3-methoxy-9-bromo-norhasubanan hydrobromide in substantially improved yields through the intermediate of the formula SPC1