cis-ethyl 2-(2-chloroacetyl)-1-phenyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate

Base Information

• Chemical Name: cis-ethyl 2-(2-chloroacetyl)-1-phenyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate
• CAS No.: 1447959-77-4
• Molecular Formula: C₂₂H₂₁ClN₂O₃
• Molecular Weight: 396.873

Synonyms:cis-ethyl 2-(2-chloroacetyl)-1-phenyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate

Chemical Property of cis-ethyl 2-(2-chloroacetyl)-1-phenyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate

Chemical Property:

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Technology Process of cis-ethyl 2-(2-chloroacetyl)-1-phenyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate

There total 3 articles about cis-ethyl 2-(2-chloroacetyl)-1-phenyl-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: 91.0%

cis-1-phenyl-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxylic acid ethyl ester (1227610-58-3) + chloroacetyl chloride (79-04-9) → cis-ethyl 2-(2-chloroacetyl)-1-phenyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate (1447959-77-4)

Guidance literature:

With sodium hydrogencarbonate; In ethyl acetate; at 0 ℃; for 0.5h;

DOI:10.1055/s-0032-1316911

Reference yield:

L-tryptophan ethyl ester (7479-05-2) → cis-ethyl 2-(2-chloroacetyl)-1-phenyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate (1447959-77-4)

Guidance literature:

Multi-step reaction with 2 steps

1: benzene / 48 h / Reflux

2: sodium hydrogencarbonate / ethyl acetate / 0.5 h / 0 °C

With sodium hydrogencarbonate; In ethyl acetate; benzene; 1: |Pictet-Spengler Synthesis;

DOI:10.1055/s-0032-1316911

Reference yield:

benzaldehyde (100-52-7) → cis-ethyl 2-(2-chloroacetyl)-1-phenyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate (1447959-77-4)

Guidance literature:

Multi-step reaction with 2 steps

1: benzene / 48 h / Reflux

2: sodium hydrogencarbonate / ethyl acetate / 0.5 h / 0 °C

With sodium hydrogencarbonate; In ethyl acetate; benzene; 1: |Pictet-Spengler Synthesis;

DOI:10.1055/s-0032-1316911

upstream raw materials:

cis-1-phenyl-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxylic acid ethyl ester

chloroacetyl chloride

L-tryptophan ethyl ester

benzaldehyde

Downstream raw materials:

cis-6-phenyl-2-propyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

C₂₄H₂₅N₃O₂

cis-2-(4-chlorobenzyl)-6-phenyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

Trans-2,3,6,7,12,12a-hexahydro-2-benzyl-6-phenyl-pyrazino[2',1';6,1]pyrido[3,4-b]indole-1,4-dione

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