Morphinan-14-ol, 4,5-alpha-epoxy-3-methoxy-

Base Information

• Chemical Name: Morphinan-14-ol, 4,5-alpha-epoxy-3-methoxy-
• CAS No.: 55256-27-4
• Deprecated CAS: 94152-63-3
• Molecular Formula: C₁₇H₂₁NO₃
• Molecular Weight: 287.359
• DSSTox Substance ID: DTXSID90203765
• Wikidata: Q76311029
• Mol file: 55256-27-4.mol

Synonyms:RAM-308;Morphinan-14-ol, 4,5-alpha-epoxy-3-methoxy-;55256-27-4;4,5-alpha-Epoxy-3-methoxymorphinan-14-ol;DTXSID90203765;LS-91963

Chemical Property of Morphinan-14-ol, 4,5-alpha-epoxy-3-methoxy-

Chemical Property:

• Vapor Pressure: 1.64E-07mmHg at 25°C
• Boiling Point: 427.4°C at 760 mmHg
• Flash Point: 174.1°C
• PSA: 50.72000
• Density: 1.25g/cm³
• LogP: 1.85580
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 271.157228913
• Heavy Atom Count: 20
• Complexity: 414

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=C2C3=C(CC4C5C3(CCN4)C(O2)CCC5)C=C1
• Isomeric SMILES: COC1=C2C3=C(C[C@@H]4[C@H]5[C@]3(CCN4)[C@@H](O2)CCC5)C=C1

Technology Process of Morphinan-14-ol, 4,5-alpha-epoxy-3-methoxy-

There total 10 articles about Morphinan-14-ol, 4,5-alpha-epoxy-3-methoxy- 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: 83.0%

C22H24Cl3NO6 (1275597-27-7) → C17H21NO3 (55256-27-4,94152-63-3)

Guidance literature:

With potassium hydroxide; In water; dimethyl sulfoxide; at 110 ℃; for 12h; Inert atmosphere;

DOI:10.1021/jo1022487

Reference yield:

C22H29NO6S (1275597-14-2) → C17H21NO3 (55256-27-4,94152-63-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium tert-butylate / tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere

2.1: lithium triethylborohydride / tetrahydrofuran / 24 h / 0 - 60 °C / Inert atmosphere

2.2: 1 h / 0 °C / Reflux

3.1: 1 h / Inert atmosphere; Reflux

4.1: potassium carbonate / 1,1,2,2-tetrachloroethane / 12 h / 150 °C / Inert atmosphere

5.1: potassium hydroxide / water; dimethyl sulfoxide / 12 h / 110 °C / Inert atmosphere

With potassium tert-butylate; lithium triethylborohydride; potassium carbonate; potassium hydroxide; In tetrahydrofuran; water; dimethyl sulfoxide; 1,1,2,2-tetrachloroethane;

DOI:10.1021/jo1022487

Reference yield:

Naltrexone (16590-41-3) → C17H21NO3 (55256-27-4,94152-63-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C

2.1: sodium tris(acetoxy)borohydride; acetic acid / 0.5 h / 0 °C / Inert atmosphere

3.1: pyridine / 0.25 h / 0 °C / Inert atmosphere

4.1: potassium tert-butylate / tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere

5.1: lithium triethylborohydride / tetrahydrofuran / 24 h / 0 - 60 °C / Inert atmosphere

5.2: 1 h / 0 °C / Reflux

6.1: 1 h / Inert atmosphere; Reflux

7.1: potassium carbonate / 1,1,2,2-tetrachloroethane / 12 h / 150 °C / Inert atmosphere

8.1: potassium hydroxide / water; dimethyl sulfoxide / 12 h / 110 °C / Inert atmosphere

With pyridine; potassium tert-butylate; sodium tris(acetoxy)borohydride; lithium triethylborohydride; potassium carbonate; acetic acid; potassium hydroxide; In tetrahydrofuran; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 1,1,2,2-tetrachloroethane;

DOI:10.1021/jo1022487

upstream raw materials:

C₂₂H₂₉NO₆S

C₂₁H₂₅NO₃

(4R,4aS,7aS,12bS)-3-(cyclopropylmethyl)-9-methoxy-1,2,3,4,5,6,7,7a-octahydro-4aH-4,12-methanobenzofuro[3,2-e]isoquinolin-4a-ol

C₂₁H₂₅NO₃

Downstream raw materials:

C₂₅H₂₇NO₅S

C₂₅H₂₇NO₆S

Refernces