50807-67-5

Usage

Uses

Used in Pharmaceutical Industry:
Morphinan-14-ol, 3-methoxyis used as a precursor in the synthesis of opioid analgesics for its potential medicinal applications. Its chemical structure allows for the production of pharmaceutical drugs with pain-relieving properties, particularly morphine and codeine, which are widely used in the treatment of moderate to severe pain.
Due to its opioid effects and potential for misuse, Morphinan-14-ol, 3-methoxyis a regulated substance, ensuring its use is limited to legitimate medical and scientific purposes. This regulation helps to mitigate the risks associated with opioid misuse and abuse while still allowing for its valuable contributions to the development of effective pain management therapies.

Upstream product

• 42281-55-0 (-)-N-Cyclobutylmethyl-14-hydroxy-3-methoxy-morphinan hydrochloride 
• 64954-57-0 (1R,4aR,8aR)-1-(4-Methoxy-benzyl)-octahydro-isoquinoline-4a,8a-diol 
• 66209-47-0 (1R,9R,10S)-N-cyclobutylformyl-9,10-dihydroxy-1-p-methoxybenzyl-decahydroisoquinoline 

Downstream Products

• 42408-82-2 Butorphanol 

Relevant academic research and scientific papers

Preparation method of butorphinol decyclobutyl impurity compound

The invention relates to the technical field of organic synthesis, and provides a preparation method of a butorphinol decyclobutyl impurity compound. The preparation of the impurity is always a difficult point in the related technical field, and the preparation of the impurity is not too long in reaction route or too low in yield. The impurity can be simply, conveniently and efficiently synthesized; a compound 1 is catalyzed by strong Lewis acid and reacts with a reducing agent to form a butorphinol decyclobutyl impurity intermediate (compound 2), and the high-purity butorphinol decyclobutyl impurity (compound 4) is obtained through cyclization reaction and demethoxylation reaction without column chromatography purification.

Process for the preparation of 14-hydroxymorphinan derivatives

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-cyclobutylmethylmorphinan has been found to possess potent agonist/antagonist activity. A new and novel total synthesis for the preparation of these compounds is described herein.

Derivatives of 9,10-dihydroxy-1-(p-alkoxybenzyl)-perhydroisoquinoline oxazine-3-one

The disclosed invention is to a compound of the formula: STR1 in which R2 is lower alkyl. These compounds are useful in the preparation of N-substituted-14-hydroxy-3-substituted morphinan derivatives which have been found to possess potent narcotic agonist or antagonist activity.

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

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.