(1R,3R)-3-(4-phenyl-1H-imidazol-2-yl)-1-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carboline

Base Information

• Chemical Name: (1R,3R)-3-(4-phenyl-1H-imidazol-2-yl)-1-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carboline
• CAS No.: 1360889-90-2
• Molecular Formula: C₂₅H₂₆N₄O
• Molecular Weight: 398.508
• Mol file: 1360889-90-2.mol

Synonyms:(1R,3R)-3-(4-phenyl-1H-imidazol-2-yl)-1-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carboline

Chemical Property of (1R,3R)-3-(4-phenyl-1H-imidazol-2-yl)-1-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carboline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3R)-3-(4-phenyl-1H-imidazol-2-yl)-1-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carboline

There total 4 articles about (1R,3R)-3-(4-phenyl-1H-imidazol-2-yl)-1-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carboline 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: 70.0%

3,4,5,6-tetrahydro-2H-pyran-4-carbaldehyde (50675-18-8) + (1R)-2-(1H-indol-3-yl)-1-(4-phenyl-1H-imidazol-2-yl)-1-ethanamine (252279-09-7) → (1S,3R)-3-(4-phenyl-1H-imidazol-2-yl)-1-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carboline (1360889-92-4) + (1R,3R)-3-(4-phenyl-1H-imidazol-2-yl)-1-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carboline (1360889-90-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃;

DOI:10.1021/ml200272z

Reference yield:

Boc-D-Trp-OH (5241-64-5) → (1S,3R)-3-(4-phenyl-1H-imidazol-2-yl)-1-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carboline (1360889-92-4) + (1R,3R)-3-(4-phenyl-1H-imidazol-2-yl)-1-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carboline (1360889-90-2)

Guidance literature:

Multi-step reaction with 4 steps

1: caesium carbonate / N,N-dimethyl-formamide / 20 °C

2: ammonium acetate / toluene / 3 h / Reflux

3: hydrogenchloride / 1,4-dioxane / 20 °C

4: trifluoroacetic acid / dichloromethane / 20 °C

With hydrogenchloride; ammonium acetate; caesium carbonate; trifluoroacetic acid; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; toluene; 4: Pictet-Spengler cyclisation;

DOI:10.1021/ml200272z

Reference yield:

tert-butyl[(1R)-2-(1H-indol-3-yl)-1-(5-phenyl-1H-imidazol-2-yl)ethyl]carbamate (335243-50-0) → (1S,3R)-3-(4-phenyl-1H-imidazol-2-yl)-1-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carboline (1360889-92-4) + (1R,3R)-3-(4-phenyl-1H-imidazol-2-yl)-1-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carboline (1360889-90-2)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / 1,4-dioxane / 20 °C

2: trifluoroacetic acid / dichloromethane / 20 °C

With hydrogenchloride; trifluoroacetic acid; In 1,4-dioxane; dichloromethane; 2: Pictet-Spengler cyclisation;

DOI:10.1021/ml200272z

upstream raw materials:

3,4,5,6-tetrahydro-2H-pyran-4-carbaldehyde

(1R)-2-(1H-indol-3-yl)-1-(4-phenyl-1H-imidazol-2-yl)-1-ethanamine

Boc-D-Trp-OH

tert-butyl[(1R)-2-(1H-indol-3-yl)-1-(5-phenyl-1H-imidazol-2-yl)ethyl]carbamate