cis-(1R,3R)-(+)-2-benzyl-3-(methoxycarbonyl)-1-<(methoxycarbonyl)ethyl>-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole

Base Information

• Chemical Name: cis-(1R,3R)-(+)-2-benzyl-3-(methoxycarbonyl)-1-<(methoxycarbonyl)ethyl>-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole
• CAS No.: 84094-75-7
• Molecular Formula: C₂₄H₂₆N₂O₄
• Molecular Weight: 406.481

Synonyms:cis-(1R,3R)-(+)-2-benzyl-3-(methoxycarbonyl)-1-<(methoxycarbonyl)ethyl>-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole

Chemical Property of cis-(1R,3R)-(+)-2-benzyl-3-(methoxycarbonyl)-1-<(methoxycarbonyl)ethyl>-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole

Chemical Property:

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Technology Process of cis-(1R,3R)-(+)-2-benzyl-3-(methoxycarbonyl)-1-<(methoxycarbonyl)ethyl>-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole

There total 4 articles about cis-(1R,3R)-(+)-2-benzyl-3-(methoxycarbonyl)-1-<(methoxycarbonyl)ethyl>-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole 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: 83.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + trans-(3R)-(-)-2-benzyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-1-propionic acid → (1S,3R)-(-)-methyl 2-benzyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate (84094-74-6) + cis-(1R,3R)-(+)-2-benzyl-3-(methoxycarbonyl)-1-<(methoxycarbonyl)ethyl>-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole (84094-75-7)

Guidance literature:

In diethyl ether; dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1021/jo000126e

Reference yield: 7.5%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (-)-2-benzyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionic acid (60702-97-8,84094-72-4,84094-73-5,91926-17-9) → (1S,3R)-(-)-methyl 2-benzyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate (84094-74-6) + cis-(1R,3R)-(+)-2-benzyl-3-(methoxycarbonyl)-1-<(methoxycarbonyl)ethyl>-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole (84094-75-7)

Guidance literature:

In methanol; diethyl ether; dichloromethane; for 1h;

DOI:10.1248/cpb.32.1313

Reference yield:

D-(+)-Nbbenzyltryptophan methyl ester (63229-68-5,73327-10-3,84094-71-3) → cis-(1R,3R)-(+)-2-benzyl-3-(methoxycarbonyl)-1-<(methoxycarbonyl)ethyl>-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole (84094-75-7)

Guidance literature:

Multi-step reaction with 2 steps

1: benzene; dioxane / 3 h / Heating

2: diethyl ether; CH₂Cl₂ / 1.) -20 deg C, 10 min, 2.) room temp., 1.5 h

In 1,4-dioxane; diethyl ether; dichloromethane; benzene;

DOI:10.1021/jo951170a

upstream raw materials:

diazomethane

(1R,3R)-(-)-2-benzyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionic acid

(-)-2-benzyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionic acid

D-(+)-N_bbenzyltryptophan methyl ester

Downstream raw materials:

(1S,3R)-(-)-methyl 2-benzyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate

trans-2-benzyl-3-carboxy-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionic acid

methyl 5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-8-carboxylate

methyl trans-2-benzyl-3-methoxycarbonyl-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate

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