5-methoxy-Nb-(methoxycarbonyl)tryptamine

Base Information

• Chemical Name: 5-methoxy-Nb-(methoxycarbonyl)tryptamine
• CAS No.: 67199-10-4
• Molecular Formula: C13H16N2O3
• Molecular Weight: 248.282
• Mol file: 67199-10-4.mol

Synonyms:5-methoxy-Nb-methoxycarbonyltryptamine;

Chemical Property of 5-methoxy-Nb-(methoxycarbonyl)tryptamine

Chemical Property:

• PSA: 63.35000
• LogP: 2.46590
• Storage Temp.: Room Temperature
• Solubility.: Dichloromethane; Methanol; DMSO; Chloroform

Purity/Quality:

METHYL N-[2-(5-METHOXY-1H-INDOL-3-YL)ETHYL]CARBAMATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-(Methoxycarbonyl)-5-methoxytryptamine is an intermediate used in the synthesis of N-Methyl-5-methoxytryptamine (M263955), which is a serotonin 5-HT2A receptor agonist.

Technology Process of 5-methoxy-Nb-(methoxycarbonyl)tryptamine

There total 10 articles about 5-methoxy-Nb-(methoxycarbonyl)tryptamine 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: 97.0%

5-methoxytryptamine hydrochloride + methyl chloroformate (79-22-1) → methyl N-[2-(5-methoxy-1H-indol-3-yl)ethyl]carbamate (67199-10-4)

Guidance literature:

With sodium hydroxide; In ethyl acetate; for 1h; Inert atmosphere;

DOI:10.1021/acs.orglett.0c00953

Reference yield: 94.0%

methanol (67-56-1) + 1-hydroxy-Nb-methoxycarbonyltryptamine (180910-53-6) → methyl N-[2-(5-methoxy-1H-indol-3-yl)ethyl]carbamate (67199-10-4)

Guidance literature:

With boron trifluoride; for 0.666667h; Heating;

DOI:10.3987/COM-00-8930

Reference yield: 90.0%

2-(5-methoxyindol-3-yl)ethylamine (608-07-1) + methyl chloroformate (79-22-1) → methyl N-[2-(5-methoxy-1H-indol-3-yl)ethyl]carbamate (67199-10-4)

Guidance literature:

With triethylamine; In dichloromethane; for 0.333333h; Ambient temperature;

DOI:10.1021/jm970210v

upstream raw materials:

2-(5-methoxyindol-3-yl)ethylamine

methyl chloroformate

methanol

1-hydroxy-N_b-methoxycarbonyltryptamine

Downstream raw materials:

(-)-norphysostigmine

Phenyl-carbamic acid (3aS,8aR)-8-benzyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-yl ester

Phenyl-carbamic acid (3aR,8aS)-8-benzyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-yl ester

Methyl-carbamic acid (3aS,8aR)-8-benzyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-yl ester

Refernces

• 1、 Zhao, Guodong,Liang, Lixin,Wang, Eryu,Lou, Shaoyan,Qi, Rui,Tong, Rongbiao. "Fenton chemistry enables the catalytic oxidative rearrangement of indoles using hydrogen peroxide". supporting information. p. 2300 - 2307. Retrieved 2021/04/12.
• 2、 Xu, Jun,Tong, Rongbiao. "An environmentally friendly protocol for oxidative halocyclization of tryptamine and tryptophol derivatives". supporting information. p. 2952 - 2956. Retrieved 2017/07/24.