2-[3-(2-Benzylamino-ethyl)-1H-indol-2-yl]-3-hydroxy-propionic acid methyl ester

Base Information

• Chemical Name: 2-[3-(2-Benzylamino-ethyl)-1H-indol-2-yl]-3-hydroxy-propionic acid methyl ester
• CAS No.: 146681-75-6
• Molecular Formula: C₂₁H₂₄N₂O₃
• Molecular Weight: 352.433
• Mol file: 146681-75-6.mol

Synonyms:2-[3-(2-Benzylamino-ethyl)-1H-indol-2-yl]-3-hydroxy-propionic acid methyl ester

Chemical Property of 2-[3-(2-Benzylamino-ethyl)-1H-indol-2-yl]-3-hydroxy-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[3-(2-Benzylamino-ethyl)-1H-indol-2-yl]-3-hydroxy-propionic acid methyl ester

There total 8 articles about 2-[3-(2-Benzylamino-ethyl)-1H-indol-2-yl]-3-hydroxy-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: 88.0%

2-[3-(2-Dibenzylamino-ethyl)-1H-indol-2-yl]-3-hydroxy-propionic acid methyl ester (146681-81-4) → 2-[3-(2-Benzylamino-ethyl)-1H-indol-2-yl]-3-hydroxy-propionic acid methyl ester (146681-75-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In acetic acid; for 1.5h;

DOI:10.1021/jo00058a025

Reference yield:

3-(2-aminoethyl)-1H-indole-2-carboxylic acid ethyl ester hydrochloride (53590-32-2) → 2-[3-(2-Benzylamino-ethyl)-1H-indol-2-yl]-3-hydroxy-propionic acid methyl ester (146681-75-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 75 percent / K₂CO₃, KI / dimethylformamide / 4 h / Ambient temperature

2: 97 percent / LiAlH₄ / tetrahydrofuran / 3.5 h / 50 - 55 °C

3: 93 percent / DMAP, pyridine / 4.5 h / Ambient temperature

4: 74 percent / dimethylsulfoxide / 1) RT, 1 h, 2) 70-73 deg C, 1 h

5: 82 percent / HCl gas / 2 h / Heating

6: 1) NaH, 2) NaBH₄, glacial acetic acid / 1) 1.5 h, reflux, 2) MeOH, -20 deg C, 1 h

7: 88 percent / H₂ / 10percent Pd/C / acetic acid / 1.5 h

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; hydrogen; sodium hydride; potassium carbonate; acetic acid; potassium iodide; palladium on activated charcoal; In tetrahydrofuran; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jo00058a025

Reference yield:

benzyl chloride (100-44-7) → 2-[3-(2-Benzylamino-ethyl)-1H-indol-2-yl]-3-hydroxy-propionic acid methyl ester (146681-75-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 75 percent / K₂CO₃, KI / dimethylformamide / 4 h / Ambient temperature

2: 97 percent / LiAlH₄ / tetrahydrofuran / 3.5 h / 50 - 55 °C

3: 93 percent / DMAP, pyridine / 4.5 h / Ambient temperature

4: 74 percent / dimethylsulfoxide / 1) RT, 1 h, 2) 70-73 deg C, 1 h

5: 82 percent / HCl gas / 2 h / Heating

6: 1) NaH, 2) NaBH₄, glacial acetic acid / 1) 1.5 h, reflux, 2) MeOH, -20 deg C, 1 h

7: 88 percent / H₂ / 10percent Pd/C / acetic acid / 1.5 h

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; hydrogen; sodium hydride; potassium carbonate; acetic acid; potassium iodide; palladium on activated charcoal; In tetrahydrofuran; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jo00058a025

upstream raw materials:

2-[3-(2-Dibenzylamino-ethyl)-1H-indol-2-yl]-3-hydroxy-propionic acid methyl ester

3-(2-aminoethyl)-1H-indole-2-carboxylic acid ethyl ester hydrochloride

benzyl chloride

N_b,N_b-dibenzyl-2-(hydroxymethyl)tryptamine

Downstream raw materials:

2,16-didehydro-3-phenyl-14,16-bis(methoxycarbonyl)-3,14-secoaspidospermidine (20α,21α)

2,16-didehydro-3-phenyl-14,16-bis(methoxycarbonyl)-3,14-secoaspidospermidine (20β,21α)

2,16-Didehydro-16,20-bis(methoxycarbonyl)-21-phenyl-20,21-seco-pseudoaspidospermidine (3α,14β,20αβ)

methyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole-5-carboxylate