methyl (1R,3R)-1-(4-chlorophenyl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate

Base Information

• Chemical Name: methyl (1R,3R)-1-(4-chlorophenyl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate
• CAS No.: 1027590-60-8
• Molecular Formula: C₂₁H₁₈Cl₂N₂O₃
• Molecular Weight: 417.292
• Mol file: 1027590-60-8.mol

Synonyms:methyl (1R,3R)-1-(4-chlorophenyl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate

Chemical Property of methyl (1R,3R)-1-(4-chlorophenyl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1R,3R)-1-(4-chlorophenyl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate

There total 3 articles about methyl (1R,3R)-1-(4-chlorophenyl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate 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: 95.0%

methyl (1R,3R)-1-(4-chlorophenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate (903575-56-4) + chloroacetyl chloride (79-04-9) → methyl (1R,3R)-1-(4-chlorophenyl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate (1027590-60-8)

Guidance literature:

With sodium hydrogencarbonate; In chloroform; at 0 ℃; Inert atmosphere;

DOI:10.1002/ardp.201000236

Reference yield:

D-tryptophan (153-94-6,27732-43-0,80206-30-0,27813-82-7) → methyl (1R,3R)-1-(4-chlorophenyl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate (1027590-60-8)

Guidance literature:

Multi-step reaction with 3 steps

1: ammonium hydroxide; acetyl chloride / Inert atmosphere

2: trifluoroacetic acid / dichloromethane / 0 - 20 °C / Inert atmosphere

3: sodium hydrogencarbonate / chloroform / 0 °C / Inert atmosphere

With ammonium hydroxide; sodium hydrogencarbonate; acetyl chloride; trifluoroacetic acid; In dichloromethane; chloroform; 2: Pictet-Spengler reaction;

DOI:10.1002/ardp.201000236

Reference yield:

D-Tryptophan methyl ester (4299-70-1,7303-49-3,22032-65-1) → methyl (1R,3R)-1-(4-chlorophenyl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate (1027590-60-8)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic acid / dichloromethane / 0 - 20 °C / Inert atmosphere

2: sodium hydrogencarbonate / chloroform / 0 °C / Inert atmosphere

With sodium hydrogencarbonate; trifluoroacetic acid; In dichloromethane; chloroform; 1: Pictet-Spengler reaction;

DOI:10.1002/ardp.201000236

upstream raw materials:

methyl (1R,3R)-1-(4-chlorophenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate

chloroacetyl chloride

D-tryptophan

D-Tryptophan methyl ester

Downstream raw materials:

(6R,12aR)-2-ethyl-6-(4-chlorophenyl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione