1-(TERT-BUTYL) 2-METHYL 1,2-INDOLINEDICARBOXYLATE

Base Information

• Chemical Name: 1-(TERT-BUTYL) 2-METHYL 1,2-INDOLINEDICARBOXYLATE
• CAS No.: 186704-03-0
• Molecular Formula: C15H19NO4
• Molecular Weight: 277.3157
• Hs Code.: 2933998090
• Mol file: 186704-03-0.mol

Synonyms:1-(TERT-BUTYL) 2-METHYL 1,2-INDOLINEDICARBOXYLATE;1-TERT-BUTYL-2-METHYLINDOLINE-1,2-DICARBOXYLATE;Ethyl indoline-2-carboxylate, N-BOC protected 97%;Methyl indoline-2-carboxylate, N-BOC protected 97%;Methyl indoline-2-carboxylate, N-BOC protected;1H-Indole-1,2-dicarboxylic acid, 2,3-dihydro-, 1-(1,1-diMethylethyl) 2-Methyl ester

Chemical Property of 1-(TERT-BUTYL) 2-METHYL 1,2-INDOLINEDICARBOXYLATE

Chemical Property:

• Vapor Pressure: 1.95E-05mmHg at 25°C
• Refractive Index: 1.536
• Boiling Point: 362.3 °C at 760 mmHg
• Flash Point: 172.9 °C
• PSA: 55.84000
• Density: 1.183 g/cm³
• LogP: 2.59080
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

98%Min ^*data from raw suppliers

Methyl indoline-2-carboxylate, N-Boc protected 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-(TERT-BUTYL) 2-METHYL 1,2-INDOLINEDICARBOXYLATE

There total 14 articles about 1-(TERT-BUTYL) 2-METHYL 1,2-INDOLINEDICARBOXYLATE 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: 92.0%

1-(1,1-dimethylethyl)-1H-indole-1,2-dicarboxylic acid 2-methyl ester (163229-48-9) → methyl (+/-)-1-t-butoxycarbonyl-indoline-2-carboxylate (186704-03-0)

Guidance literature:

With methanol; magnesium; at 0 ℃; for 4h;

DOI:10.1246/bcsj.77.1021

Reference yield: 69.0%

di-tert-butyl dicarbonate (24424-99-5) + indoline-2-carboxylic acid methyl ester (59040-84-5,130791-93-4,141410-06-2) → methyl (+/-)-1-t-butoxycarbonyl-indoline-2-carboxylate (186704-03-0)

Guidance literature:

at 20 ℃; for 40h;

DOI:10.1246/bcsj.77.1021

Reference yield: 64.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + carbon dioxide (124-38-9,18923-20-1) + indole-1-carboxylic acid tert-butyl ester (75400-67-8) → C17H21NO6 + methyl (+/-)-1-t-butoxycarbonyl-indoline-2-carboxylate (186704-03-0)

Guidance literature:

carbon dioxide; indole-1-carboxylic acid tert-butyl ester; With tetrabutylammonium bromide; In water monomer; N,N-dimethyl-formamide; at 20 ℃; Electrolysis;

doazomethane; In diethyl ether; for 0.166667h; diastereoselective reaction;

DOI:10.1021/jacs.1c13032

upstream raw materials:

1-(1,1-dimethylethyl)-1H-indole-1,2-dicarboxylic acid 2-methyl ester

di-tert-butyl dicarbonate

indoline-2-carboxylic acid methyl ester

indole-2-carboxylic acid methyl ester

Downstream raw materials:

2-cyclohexyl-2-{1-[3,3-difluoro-1-(hydroxy-methoxycarbonyl-methyl)-propylcarbamoyl]-3-methyl-butylcarbamoyl}-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

2-(1-benzyloxycarbonyl-3-methyl-butylcarbamoyl)-2-cyclohexyl-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

N-{[1-(tert-butoxycarbonyl)-2-cyclohexyl-2,3-dihydro-1H-indol-2-yl]carbonyl}-L-leucine

2-(5-chloro-thiophen-2-ylmethyl)-2,3-dihydro-indole-1,2-dicarboxylic acid 1-tert-butyl ester

Refernces

• 1、 Kondoh, Azusa,Ojima, Rihaku,Terada, Masahiro. "Formal Fluorinative Ring Opening of 2-Benzoylpyrrolidines Utilizing [1,2]-Phospha-Brook Rearrangement for Synthesis of 2-Aryl-3-fluoropiperidines". supporting information. p. 7894 - 7899. Retrieved 2021/10/20.
• 2、 Gilmore, Christopher D.,Allan, Kevin M.,Stoltz, Brian M.. "Orthogonal synthesis of indolines and isoquinolines via aryne annulation". . p. 1558 - 1559. Retrieved 2008/09/17.