4-[3-[(6R,12aR)-6-benzo[1,3]dioxol-5-yl-1,4-dioxo-3,4,6,7,12,12a-hexahydro-1H-pyrazino[1',2':1,6]pyrido[3,4-b]indol-2-yl]benzyl]piperazine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 4-[3-[(6R,12aR)-6-benzo[1,3]dioxol-5-yl-1,4-dioxo-3,4,6,7,12,12a-hexahydro-1H-pyrazino[1',2':1,6]pyrido[3,4-b]indol-2-yl]benzyl]piperazine-1-carboxylic acid tert-butyl ester
• CAS No.: 1295647-22-1
• Molecular Formula: C₃₇H₃₉N₅O₆
• Molecular Weight: 649.747

Synonyms:4-[3-[(6R,12aR)-6-benzo[1,3]dioxol-5-yl-1,4-dioxo-3,4,6,7,12,12a-hexahydro-1H-pyrazino[1',2':1,6]pyrido[3,4-b]indol-2-yl]benzyl]piperazine-1-carboxylic acid tert-butyl ester

Chemical Property of 4-[3-[(6R,12aR)-6-benzo[1,3]dioxol-5-yl-1,4-dioxo-3,4,6,7,12,12a-hexahydro-1H-pyrazino[1',2':1,6]pyrido[3,4-b]indol-2-yl]benzyl]piperazine-1-carboxylic acid tert-butyl ester

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Technology Process of 4-[3-[(6R,12aR)-6-benzo[1,3]dioxol-5-yl-1,4-dioxo-3,4,6,7,12,12a-hexahydro-1H-pyrazino[1',2':1,6]pyrido[3,4-b]indol-2-yl]benzyl]piperazine-1-carboxylic acid tert-butyl ester

There total 5 articles about 4-[3-[(6R,12aR)-6-benzo[1,3]dioxol-5-yl-1,4-dioxo-3,4,6,7,12,12a-hexahydro-1H-pyrazino[1',2':1,6]pyrido[3,4-b]indol-2-yl]benzyl]piperazine-1-carboxylic acid tert-butyl 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: 23.0%

4-[(3-iodophenyl)methyl]-1-piperazinecarboxylic acid 1,1-dimethylethyl ester (850375-09-6) + (6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione (171596-36-4) → 4-[3-[(6R,12aR)-6-benzo[1,3]dioxol-5-yl-1,4-dioxo-3,4,6,7,12,12a-hexahydro-1H-pyrazino[1',2':1,6]pyrido[3,4-b]indol-2-yl]benzyl]piperazine-1-carboxylic acid tert-butyl ester (1295647-22-1)

Guidance literature:

With potassium phosphate; copper(l) iodide; trans-1,2-Diaminocyclohexane; In 1,4-dioxane; at 14 ℃; for 336h;

DOI:10.1021/jm1014617

Reference yield:

piperonal (120-57-0,30024-74-9) → 4-[3-[(6R,12aR)-6-benzo[1,3]dioxol-5-yl-1,4-dioxo-3,4,6,7,12,12a-hexahydro-1H-pyrazino[1',2':1,6]pyrido[3,4-b]indol-2-yl]benzyl]piperazine-1-carboxylic acid tert-butyl ester (1295647-22-1)

Guidance literature:

Multi-step reaction with 4 steps

1: trifluoroacetic acid / dichloromethane / 24 h / 0 - 20 °C / Molecular sieve

2: triethylamine / chloroform / -10 °C

3: ammonia / methanol / Reflux

4: copper(l) iodide; potassium phosphate; trans-1,2-Diaminocyclohexane / 1,4-dioxane / 336 h / 14 °C

With potassium phosphate; copper(l) iodide; trans-1,2-Diaminocyclohexane; ammonia; triethylamine; trifluoroacetic acid; In 1,4-dioxane; methanol; dichloromethane; chloroform; 1: Pictet-Spengler cyclisation;

DOI:10.1021/jm1014617

Reference yield:

methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate (171489-59-1) → 4-[3-[(6R,12aR)-6-benzo[1,3]dioxol-5-yl-1,4-dioxo-3,4,6,7,12,12a-hexahydro-1H-pyrazino[1',2':1,6]pyrido[3,4-b]indol-2-yl]benzyl]piperazine-1-carboxylic acid tert-butyl ester (1295647-22-1)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonia / methanol / Reflux

2: copper(l) iodide; potassium phosphate; trans-1,2-Diaminocyclohexane / 1,4-dioxane / 336 h / 14 °C

With potassium phosphate; copper(l) iodide; trans-1,2-Diaminocyclohexane; ammonia; In 1,4-dioxane; methanol;

DOI:10.1021/jm1014617

upstream raw materials:

4-[(3-iodophenyl)methyl]-1-piperazinecarboxylic acid 1,1-dimethylethyl ester

(6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

piperonal

D-Tryptophan methyl ester

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