4-[3-(3-methoxycarbonylmethyl-indol-1-yl)-propyl]-piperidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: 4-[3-(3-methoxycarbonylmethyl-indol-1-yl)-propyl]-piperidine-1-carboxylic acid benzyl ester
• CAS No.: 461052-26-6
• Molecular Formula: C₂₇H₃₂N₂O₄
• Molecular Weight: 448.562

Synonyms:4-[3-(3-methoxycarbonylmethyl-indol-1-yl)-propyl]-piperidine-1-carboxylic acid benzyl ester

Chemical Property of 4-[3-(3-methoxycarbonylmethyl-indol-1-yl)-propyl]-piperidine-1-carboxylic acid benzyl ester

Chemical Property:

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Technology Process of 4-[3-(3-methoxycarbonylmethyl-indol-1-yl)-propyl]-piperidine-1-carboxylic acid benzyl ester

There total 2 articles about 4-[3-(3-methoxycarbonylmethyl-indol-1-yl)-propyl]-piperidine-1-carboxylic acid benzyl 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: 55.0%

Indole-3-acetic acid methyl ester (1912-33-0) + 3-(1-benzyloxycarbonyl-4-piperidyl)propyl iodide (120426-40-6) → 4-[3-(3-methoxycarbonylmethyl-indol-1-yl)-propyl]-piperidine-1-carboxylic acid benzyl ester (461052-26-6)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/S0223-5234(01)01325-3

Reference yield:

benzyl 4-(2-hydroxypropyl)-1-piperidinecarboxylate (99198-80-8) → 4-[3-(3-methoxycarbonylmethyl-indol-1-yl)-propyl]-piperidine-1-carboxylic acid benzyl ester (461052-26-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / triphenylphosphine; imidazole; iodine / toluene; acetonitrile / 3 h / 20 °C

2: 55 percent / NaH / dimethylformamide / 20 °C

With 1H-imidazole; iodine; sodium hydride; triphenylphosphine; In N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0223-5234(01)01325-3

Reference yield: 80.0%

4-[3-(3-methoxycarbonylmethyl-indol-1-yl)-propyl]-piperidine-1-carboxylic acid benzyl ester (461052-26-6) → 4-[3-(3-carboxymethyl-indol-1-yl)-propyl]-piperidine-1-carboxylic acid benzyl ester (461052-34-6)

Guidance literature:

With lithium hydroxide; In methanol; at 20 ℃;

DOI:10.1016/S0223-5234(01)01325-3

upstream raw materials:

Indole-3-acetic acid methyl ester

3-(1-benzyloxycarbonyl-4-piperidyl)propyl iodide

benzyl 4-(2-hydroxypropyl)-1-piperidinecarboxylate

Downstream raw materials:

4-[3-(3-carboxymethyl-indol-1-yl)-propyl]-piperidine-1-carboxylic acid benzyl ester

4-(3-{3-[(2-ethoxycarbonyl-ethylcarbamoyl)-methyl]-indol-1-yl}-propyl)-piperidine-1-carboxylic acid benzyl ester

3-{2-[1-(3-piperidin-4-yl-propyl)-1H-indol-3-yl]-acetylamino}-2-(toluene-4-sulfonylamino)-propionic acid methyl ester

3-{[2-(1-{3-[1-(tert-butyloxycarbonyl)-4-piperidyl]propyl}-1H-3-indolyl)acetyl]amino}-2-{[(4-methyl-phenyl)sulfonyl]amino}propanoic acid

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