trans-N_b-benzyl-3-(ethoxycarbonyl)-6-methoxy-9-methyltetrahydro-β-carboline-1-propionic acid methyl ester

Base Information

• Chemical Name: trans-N_b-benzyl-3-(ethoxycarbonyl)-6-methoxy-9-methyltetrahydro-β-carboline-1-propionic acid methyl ester
• CAS No.: 409095-10-9
• Molecular Formula: C₂₇H₃₂N₂O₅
• Molecular Weight: 464.561

Synonyms:trans-N_b-benzyl-3-(ethoxycarbonyl)-6-methoxy-9-methyltetrahydro-β-carboline-1-propionic acid methyl ester

Chemical Property of trans-N_b-benzyl-3-(ethoxycarbonyl)-6-methoxy-9-methyltetrahydro-β-carboline-1-propionic acid methyl ester

Chemical Property:

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Technology Process of trans-N_b-benzyl-3-(ethoxycarbonyl)-6-methoxy-9-methyltetrahydro-β-carboline-1-propionic acid methyl ester

There total 22 articles about trans-N_b-benzyl-3-(ethoxycarbonyl)-6-methoxy-9-methyltetrahydro-β-carboline-1-propionic acid methyl ester 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: 82.0%

4-oxobutanoic acid methyl ester (13865-19-5) + Nb-benzyl-5-methoxy-1-methyl-D-tryptophan ethyl ester (600135-96-4) → trans-Nb-benzyl-3-(ethoxycarbonyl)-6-methoxy-9-methyltetrahydro-β-carboline-1-propionic acid methyl ester (409095-10-9)

Guidance literature:

4-oxobutanoic acid methyl ester; N_b-benzyl-5-methoxy-1-methyl-D-tryptophan ethyl ester; With acetic acid; In dichloromethane; at 20 ℃;

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 240h;

DOI:10.1021/jo030055u

Reference yield: 56.0%

(1S,3R)-ethyl 2-benzyl-5-iodo-6-methoxy-1-(3-methoxy-3-oxopropyl)-9-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]-indole-3-carboxylate (1443744-15-7) + bis(pinacol)diborane (73183-34-3) → (1S,3R)-ethyl 2-benzyl-6-methoxy-1-(3-methoxy-3-oxopropyl)-9-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate (1443744-19-1) + trans-Nb-benzyl-3-(ethoxycarbonyl)-6-methoxy-9-methyltetrahydro-β-carboline-1-propionic acid methyl ester (409095-10-9)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In dimethyl sulfoxide; at 100 ℃; for 10h; Inert atmosphere; Sealed tube;

DOI:10.1021/jo400469t

Reference yield: 38.0%

(1S,3R)-ethyl 2-benzyl-6-methoxy-1-(3-methoxy-3-oxopropyl)-9-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate (1443744-19-1) + (1S,3R)-ethyl 2-benzyl-5-iodo-6-methoxy-1-(3-methoxy-3-oxopropyl)-9-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]-indole-3-carboxylate (1443744-15-7) → (1R,1′R,3S,3′S)-diethyl 2,2′-dibenzyl-6,6′-dimethoxy-1,1′-bis(3-methoxy-3-oxopropyl)-9,9′-dimethyl-2,2′,3,3′,4,4′,9,9′-octahydro-1H,1′H-[5,5′-bipyrido[3,4-b]indole]-3,3′-dicarboxylate + (1S,1'S,3R,3'R)-diethyl 2,2'-dibenzyl-6,6'-dimethoxy-1,1'-bis(3-methoxy-3-oxopropyl)-9,9'-dimethyl-2,2',3,3',4,4',9,9'-octahydro-1H,1'H-[5,5'-bipyrido[3,4-b]indole]-3,3'-dicarboxylate + trans-Nb-benzyl-3-(ethoxycarbonyl)-6-methoxy-9-methyltetrahydro-β-carboline-1-propionic acid methyl ester (409095-10-9)

Guidance literature:

With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl; In tetrahydrofuran; water; at 50 ℃; for 48h; Reagent/catalyst; Time; Inert atmosphere; Sealed tube;

DOI:10.1021/jo400469t

upstream raw materials:

4-oxobutanoic acid methyl ester

N_b-benzyl-5-methoxy-1-methyl-D-tryptophan ethyl ester

5-methoxy-3-methyl-1H-indole

5-methoxy-3-methyl-1H-indole-2-carboxylic acid

Downstream raw materials:

(6S,10S)-methyl-2-methoxy-5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]indole-8-carboxylate

C₂₃H₂₄N₂O₂

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