(5S,10R)-(+)-3-bromo-10,11-dihydro-5-methyl-5H-dibenzocyclohepten-5,10-imine

Base Information

• Chemical Name: (5S,10R)-(+)-3-bromo-10,11-dihydro-5-methyl-5H-dibenzocyclohepten-5,10-imine
• CAS No.: 125134-28-3
• Molecular Formula: C₁₆H₁₄BrN
• Molecular Weight: 300.198
• Mol file: 125134-28-3.mol

Synonyms:

Chemical Property of (5S,10R)-(+)-3-bromo-10,11-dihydro-5-methyl-5H-dibenzocyclohepten-5,10-imine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,10R)-(+)-3-bromo-10,11-dihydro-5-methyl-5H-dibenzocyclohepten-5,10-imine

There total 8 articles about (5S,10R)-(+)-3-bromo-10,11-dihydro-5-methyl-5H-dibenzocyclohepten-5,10-imine 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: 45.0%

(+)-dizocilpine (70449-94-4,77086-18-1,77086-19-2,77086-21-6) → (5S,10R)-(+)-3-bromo-10,11-dihydro-5-methyl-5H-dibenzocyclohepten-5,10-imine (125134-28-3)

Guidance literature:

With N-Bromosuccinimide; sulfuric acid; In water; Ambient temperature; overnight;

DOI:10.1021/jm00164a052

Reference yield:

(5S,10R)-L-phenylalanyl-3-bromo-10,11-dihydro-5-methyl-5H-dibenzocyclohepten-5,10-imine (125049-28-7) → (5S,10R)-(+)-3-bromo-10,11-dihydro-5-methyl-5H-dibenzocyclohepten-5,10-imine (125134-28-3)

Guidance literature:

With phenyl isothiocyanate; In dichloromethane; Heating;

DOI:10.1021/jm00164a052

Reference yield:

3-bromo-10,11-dihydro-5-methyl-5H-dibenzo[a,d]-cyclohepten-5,10-imine (111305-45-4) → (5S,10R)-(+)-3-bromo-10,11-dihydro-5-methyl-5H-dibenzocyclohepten-5,10-imine (125134-28-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.9 g / diisopropylethylamine (DIPEA), bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BOP-Cl) / CH₂Cl₂ / 120 h / 0 - 5 °C

2: 1.23 g / trifluoroacetic acid / CH₂Cl₂ / 0.5 h / 0 °C

3: 0.638 g / phenyl isothiocyanate / CH₂Cl₂ / Heating

With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; phenyl isothiocyanate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jm00164a052

upstream raw materials:

(+)-dizocilpine

(5S,10R)-L-phenylalanyl-3-bromo-10,11-dihydro-5-methyl-5H-dibenzocyclohepten-5,10-imine

3-bromo-10,11-dihydro-5-methyl-5H-dibenzo[a,d]-cyclohepten-5,10-imine

12-hydroxy-3-bromo-5-methyl-10,11-dihydro-5H-dibenzocyclohepten-5,10-imine

Refernces