3-[2-(t-butyloxycarbonylamino)ethyl]-5-hydroxy-1H-indole

Base Information

• Chemical Name: 3-[2-(t-butyloxycarbonylamino)ethyl]-5-hydroxy-1H-indole
• CAS No.: 53157-48-5
• Molecular Formula: C15H20N2O3
• Molecular Weight: 276.335
• Mol file: 53157-48-5.mol

Synonyms:N-tert-Butyloxycarbonyl Serotonin;

Chemical Property of 3-[2-(t-butyloxycarbonylamino)ethyl]-5-hydroxy-1H-indole

Chemical Property:

• Melting Point: >125°C (dec.)
• PSA: 74.35000
• LogP: 3.33160
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Dichloromethane, DMSO (Slightly), Ethyl Acetate, Methanol

Purity/Quality:

98% or more ^*data from raw suppliers

N-tert-Butyloxycarbonyl Serotonin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-tert-Butyloxycarbonyl Serotonin is a protected serotonin (S274980), a monoamine neurotransmitter.It is used in the preparation of protein kinase inhibitors and receptor agonists.

Technology Process of 3-[2-(t-butyloxycarbonylamino)ethyl]-5-hydroxy-1H-indole

There total 11 articles about 3-[2-(t-butyloxycarbonylamino)ethyl]-5-hydroxy-1H-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: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + serotonin hydrochloride (153-98-0,21591-86-6) → tert-butyl 2-(5-hydroxy-1H-indol-3-yl)ethylcarbamate (53157-48-5)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1016/j.bmc.2010.04.001

Reference yield: 97.8%

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) + serotonin hydrochloride (153-98-0,21591-86-6) → tert-butyl 2-(5-hydroxy-1H-indol-3-yl)ethylcarbamate (53157-48-5)

Guidance literature:

With TEA; In 1,4-dioxane; water; at 45 ℃; for 1h;

DOI:10.1021/jm00089a015

Reference yield: 95.0%

di-tert-butyl dicarbonate (24424-99-5) + serotonin creatinine sulfate (971-74-4) → tert-butyl 2-(5-hydroxy-1H-indol-3-yl)ethylcarbamate (53157-48-5)

Guidance literature:

With sodium hydroxide; for 1h; Ambient temperature;

DOI:10.1021/jm00018a020

upstream raw materials:

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

serotonin hydrochloride

di-tert-butyl dicarbonate

serotonin creatinine sulfate

Downstream raw materials:

2-(4-{2-[3-(2-{N-tert-Butoxycarbonyl}aminoethyl)-1H-indol-5-yloxy]acetyl}piperazin-1-yl)benzonitrile

[2-(5-{2-[4-(2-Nitro-phenyl)-piperazin-1-yl]-2-oxo-ethoxy}-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester

[2-(5-{4-[4-(4-Nitro-phenyl)-piperazin-1-yl]-4-oxo-butoxy}-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester

5-[3-(2-{N-tert-Butoxycarbonyl}aminoethyl)-1H-indol-5-yloxy]-1-[4-(4-nitrophenyl)piperazin-1-yl]pentan-1-one

Refernces

• 1、 Dai, Zhipeng,Chauhan, Sitara,Green, Thomas K.. "Synthesis and enantioseparation of atropisomers of serotonin dimer". . p. 4022 - 4024. Retrieved 2015.
• 2、 Li, Qiuhan,Levi, Samuel M.,Jacobsen, Eric N.. "Highly Selective β-Mannosylations and β-Rhamnosylations Catalyzed by Bis-thiourea". supporting information. p. 11865 - 11872. Retrieved 2020/08/06.