(5α)-4,5-Epoxy-3,14-dihydroxy-17-(2-propenyl)-Morphinan-6-one Cyclic 1,2-Ethanediyl Acetal

Base Information

• Chemical Name: (5α)-4,5-Epoxy-3,14-dihydroxy-17-(2-propenyl)-Morphinan-6-one Cyclic 1,2-Ethanediyl Acetal
• CAS No.: 646032-89-5
• Molecular Formula: C₂₁H₂₅NO₅
• Molecular Weight: 371.433
• Mol file: 646032-89-5.mol

Synonyms:4,5α-epoxy-3,14β-dihydroxy-17-(prop-2-enyl)-morphinane-6-spiro-2’-(1,3-dioxolan)

Chemical Property of (5α)-4,5-Epoxy-3,14-dihydroxy-17-(2-propenyl)-Morphinan-6-one Cyclic 1,2-Ethanediyl Acetal

Chemical Property:

Purity/Quality:

(5α)-4,5-Epoxy-3,14-dihydroxy-17-(2-propenyl)-morphinan-6-oneCyclic1,2-EthanediylAcetal ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (5α)-4,5-Epoxy-3,14-dihydroxy-17-(2-propenyl)-Morphinan-6-one Cyclic 1,2-Ethanediyl Acetal is a reactant used in the preparation of carboxamido-substituted opioids.

Technology Process of (5α)-4,5-Epoxy-3,14-dihydroxy-17-(2-propenyl)-Morphinan-6-one Cyclic 1,2-Ethanediyl Acetal

There total 6 articles about (5α)-4,5-Epoxy-3,14-dihydroxy-17-(2-propenyl)-Morphinan-6-one Cyclic 1,2-Ethanediyl Acetal which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

naloxone hydrochloride (357-08-4) + ethylene glycol (107-21-1) → 4,5α-epoxy-3,14β-dihydroxy-17-(prop-2-enyl)-morphinane-6-spiro-2’-(1,3-dioxolan) (646032-89-5)

Guidance literature:

With methanesulfonic acid; at 80 - 90 ℃; for 18h;

Reference yield: 79.0%

Naloxone (465-65-6) + ethylene glycol (107-21-1) → 4,5α-epoxy-3,14β-dihydroxy-17-(prop-2-enyl)-morphinane-6-spiro-2’-(1,3-dioxolan) (646032-89-5)

Guidance literature:

Naloxone; ethylene glycol; With toluene-4-sulfonic acid; In toluene; for 18h; Reflux; Dean-Stark;

With hydrogenchloride; sodium hydroxide; In dichloromethane; water; pH=7 - 9;

DOI:10.1021/acs.oprd.1c00288

Reference yield: 46.0%

(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 (1449113-80-7) + vinyl magnesium bromide (1826-67-1) → 4,5α-epoxy-3,14β-dihydroxy-17-(prop-2-enyl)-morphinane-6-spiro-2’-(1,3-dioxolan) (646032-89-5)

Guidance literature:

In tetrahydrofuran; at 0 - 20 ℃; for 2h;

DOI:10.1002/adsc.201300284

upstream raw materials:

naloxone hydrochloride

ethylene glycol

(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

(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

Downstream raw materials:

Naloxone

3-benzyloxy-4,5α-epoxy-14β-hydroxy-17-(prop-2-enyl)-morphinane-6-spiro-2'-(1,3-dioxolan)

Refernces

• 1、 Endoma-Arias, Mary Ann A.,Cox, D. Phillip,Hudlicky, Tomas. "General method of synthesis for naloxone, naltrexone, nalbuphone, and nalbuphine by the reaction of grignard reagents with an oxazolidine derived from oxymorphone". . p. 1869 - 1873. Retrieved 2013/07/19.
• 2、 -. "MORPHINAN DERIVATIVES THE QUATERNARY AMMONIUM SALTS THEREOF SUBSTITUTED IN POSITION 14, METHOD FOR PRODUCTION AND USE THEREOF". Page/Page column 52-53. . Retrieved 2010/02/06.