646032-89-5

Usage

Uses

Used in Pharmaceutical Industry:
(5α)-4,5-Epoxy-3,14-dihydroxy-17-(2-propenyl)-Morphinan-6-one Cyclic 1,2-Ethanediyl Acetal is used as a reactant for the synthesis of carboxamido-substituted opioids. These opioids are essential in the development of potent analgesic medications, which are crucial for managing severe pain and providing relief to patients suffering from various conditions.
As a key component in the production of these medications, (5α)-4,5-Epoxy-3,14-dihydroxy-17-(2-propenyl)-Morphinan-6-one Cyclic 1,2-Ethanediyl Acetal plays a significant role in the pharmaceutical industry, contributing to the development and advancement of pain management treatments.

Upstream product

• 357-08-4 naloxone hydrochloride 
• 107-21-1 ethylene glycol 
• 1407592-43-1 (5aR,8aS,11aR,11bS)-2-acetoxy-5,5a,9,10-tetrahydro-6,11b-ethano-7Hfuro[2',3',4',5':4,5]phenanthro[9,8a-d]oxazol-11(11aH)-one 
• 1449113-80-7 (5aR,6R,8aS,11aR,11bS)-2-acetoxy-5,5a,9,10-tetrahydro-11(11aH)-spiro-2-(1,3-dioxolan)-6,11b-ethano-7H-furo[2',3‘,4‘,5 ‘:4,5]phenanthro[9,8a-d]oxazole 
• 1826-67-1 vinyl magnesium bromide 
• 76-41-5 oxymorphone 
• 75660-23-0 3-acetyloxymorphone 
• 465-65-6 Naloxone 

Downstream Products

• 646032-91-9 3-benzyloxy-4,5α-epoxy-14β-hydroxy-17-(prop-2-enyl)-morphinane-6-spiro-2'-(1,3-dioxolan) 
• 465-65-6 Naloxone 

Relevant academic research and scientific papers

Synthesis of 1-Chloronaloxone and 2-Chloronaloxone

This paper describes the unambiguous synthesis of authentic samples of 1-chloronaloxone and 2-chloronaloxone to support the unequivocal assignment of impurities observed in a drug product containing a combination of buprenorphine hydrochloride and naloxone hydrochloride. The key step in the synthesis of 1-chloronaloxone was the C-1-selective chlorination of (5α)-6-(1,3-dioxolan-2-yl)-4,5-epoxy-14-hydroxy-3-methoxy-17-(2-propenyl)morphinan using the Palau’Chlor reagent. The key step in the synthesis of 2-chloronaloxone was the C-2-selective chlorination of (5α)-3-diethylcarbamate-6-(1,3-dioxolan-2-yl)-4,5-epoxy-14-hydroxy-17-(2-propenyl)morphinan using a directed ortho metalation approach.

General method of synthesis for naloxone, naltrexone, nalbuphone, and nalbuphine by the reaction of grignard reagents with an oxazolidine derived from oxymorphone

The N-oxide of O-acyloxymorphone, when treated with the Burgess reagent, provides the corresponding oxazolidine in a one-pot sequence and in excellent yield. The oxazolidine derived from oxymorphone, temporarily protected at O-3 and C-6, reacts with Grignard reagents to provide directly N-allyl, N-cyclopropylmethyl, and N-cyclobutylmethyl derivatives that are further converted to the title compounds, namely naltrexone, naloxone, nalbuphone, and nalbuphine in excellent yields. Each of these medicinal agents is obtained from the oxazolidine in a one-pot sequence. Complete spectral and experimental data are provided for all compounds. Copyright

PROCESS FOR THE PREPARATION OF MORPHINE ANALOGS VIA THE REACTION OF ORGANOMETALLIC REAGENTS WITH AN OXAZOLIDINE DERIVED FROM MORPHINANS

The oxazolidine derived from the reaction of oxymorphone with the Burgess reagent, temporariiy protected at 0-3 and C-6, reacts with Grignard or other suitable metallic or organometallic reagents to directly provide, for example, A/-allyl, A/-methylcyclopropyl and /V-methylcyclobutyl derivatives that are further converted into naltrexone, naloxone, nalbuphone and nalbuphine in excellent yields. These morphine analogs can be prepared from the oxazolidine in a one- pot synthesis.

MORPHINAN DERIVATIVES THE QUATERNARY AMMONIUM SALTS THEREOF SUBSTITUTED IN POSITION 14, METHOD FOR PRODUCTION AND USE THEREOF

The invention relates to a class of morphinan compounds and the quaternary ammonium salts thereof, substituted in position 14, which may be used as highly-active analgesics or also as opioid antagonists. The invention further relates to the pharmaceutically-acceptable salts and easily-produced derivatives thereof, a process for production thereof and use thereof in the production of pharmaceutical specialities.