N-Desmethyl N-Ethoxycarbonyl Dextrorphan

Base Information

• Chemical Name: N-Desmethyl N-Ethoxycarbonyl Dextrorphan
• CAS No.: 1079043-47-2
• Molecular Formula: C₁₉H₂₅NO₃
• Molecular Weight: 315.412
• Mol file: 1079043-47-2.mol

Synonyms:N-Desmethyl N-Ethoxycarbonyl Dextrorphan;3-Hydroxy-(9α,13α,14α)-Morphinan-17-carboxylic Acid Ethyl Ester

Chemical Property of N-Desmethyl N-Ethoxycarbonyl Dextrorphan

Chemical Property:

• PSA: 49.77000
• LogP: 3.54500

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A derivative of dextrorphan

Technology Process of N-Desmethyl N-Ethoxycarbonyl Dextrorphan

There total 7 articles about N-Desmethyl N-Ethoxycarbonyl Dextrorphan 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: 93.0%

(4bS,8aS,9S)-ethyl 3-methoxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-11-carboxylate (524713-55-1) → (4bS,8aS,9S)-ethyl 3-hydroxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-11-carboxylate (1079043-47-2)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 - 20 ℃; for 1h; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.joc.0c00125

Reference yield:

chloroformic acid ethyl ester (541-41-3) + (+)-dextrorphan (125-73-5) → (4bS,8aS,9S)-ethyl 3-hydroxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-11-carboxylate (1079043-47-2)

Guidance literature:

With potassium carbonate; In chloroform; at 70 ℃;

DOI:10.1021/cn400205z

Reference yield:

dextromethorphan hydrobromide → (4bS,8aS,9S)-ethyl 3-hydroxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-11-carboxylate (1079043-47-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: ammonium hydroxide / 1 h / 20 °C

1.2: Reflux

2.1: boron tribromide / dichloromethane / 0 - 5 °C

With ammonium hydroxide; boron tribromide; In dichloromethane;

DOI:10.1080/00304948.2015.1025015

upstream raw materials:

(4bS,8aS,9S)-ethyl 3-methoxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-11-carboxylate

chloroformic acid ethyl ester

(+)-dextrorphan

Levomethorphan

Downstream raw materials:

(+)-3-Hydroxymorphinan

(+)-MCL-740

Dimemorfan

Dimemorfan phosphate

Refernces

• 1、 Liu, Hui,Zheng, Wen-Yue,Ou, Xian-Fei,Ju, Xiu-Lian. "An efficient synthesis of dimemorfan from dextromethorphan". . p. 214 - 219. Retrieved 2015.
• 2、 -. "COMBINATION OF MORPHINAN COMPOUNDS AND ANTIDEPRESSANT FOR THE TREATMENT OF PSEUDOBULBAR AFFECT, NEUROLGICAL DISEASES, INTRACTABLE AND CHRONIC PAIN AND BRAIN INJURY". . . Retrieved 2016/06/09.