tert-Butyl 4-oxo-4,5,6,7-tetrahydro-1H-indole-1-carboxylate

Base Information

• Chemical Name: tert-Butyl 4-oxo-4,5,6,7-tetrahydro-1H-indole-1-carboxylate
• CAS No.: 877170-76-8
• Molecular Formula: C13H17NO3
• Molecular Weight: 235.283
• DSSTox Substance ID: DTXSID00701727
• Wikidata: Q72503940
• Mol file: 877170-76-8.mol

Synonyms:tert-Butyl 4-oxo-4,5,6,7-tetrahydro-1H-indole-1-carboxylate;877170-76-8;tert-butyl 4-oxo-6,7-dihydro-5H-indole-1-carboxylate;SCHEMBL1692228;DTXSID00701727;XRYXQDYFSBOZFJ-UHFFFAOYSA-N;CKB17076;CS-M3342;CS-15012;EN300-6478539;Z1508715278;tert-butyl 4,5,6,7-tetrahydro-4-oxoindole-1-carboxylate;tert-butyl 4-oxo-4,5,6,7-tetrahydroindole-1-carboxylate;tert-Butyl4-oxo-4,5,6,7-tetrahydro-1H-indole-1-carboxylate;1,5,6,7-tetrahydro-indol-4-one-1-carboxylic acid tert-butyl ester

Chemical Property of tert-Butyl 4-oxo-4,5,6,7-tetrahydro-1H-indole-1-carboxylate

Chemical Property:

• Melting Point: 79-80℃
• Density: 1.17
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 235.12084340
• Heavy Atom Count: 17
• Complexity: 332

Purity/Quality:

97% ^*data from raw suppliers

tert-Butyl4-oxo-4,5,6,7-tetrahydro-1H-indole-1-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C=CC2=C1CCCC2=O

Technology Process of tert-Butyl 4-oxo-4,5,6,7-tetrahydro-1H-indole-1-carboxylate

There total 4 articles about tert-Butyl 4-oxo-4,5,6,7-tetrahydro-1H-indole-1-carboxylate 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%

1,5,6,7-tetrahydro-indol-4-one (13754-86-4) + di-tert-butyl dicarbonate (24424-99-5) → 4-oxo-4,5,6,7-tetrahydro-indole-1-carboxylic acid tert-butyl ester (877170-76-8)

Guidance literature:

With dmap; In acetonitrile; at 20 ℃;

DOI:10.1021/ja057768+

Reference yield: 26.0%

Tert-butyl 4-((R,E)-4-(methoxycarbonyl)but-3-en-2-yl)-1H-indole-1-carboxylate (877170-89-3) + Isopropenyl acetate (108-22-5) → 4-oxo-4,5,6,7-tetrahydro-indole-1-carboxylic acid tert-butyl ester (877170-76-8)

Guidance literature:

With toluene-4-sulfonic acid; for 5h; Heating / reflux;

Reference yield:

1,3-cylohexanedione (504-02-9) → 4-oxo-4,5,6,7-tetrahydro-indole-1-carboxylic acid tert-butyl ester (877170-76-8)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran; toluene / Dean-Stark; Reflux

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1-bromo-2,3,4-trimethylbenzene; potassium carbonate / N,N-dimethyl-formamide / 2 h / 150 °C / Inert atmosphere

3: N,N-dimethylamino-pyridine; N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; N,N-dimethylamino-pyridine; 1-bromo-2,3,4-trimethylbenzene; potassium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; acetonitrile;

upstream raw materials:

1,5,6,7-tetrahydro-indol-4-one

di-tert-butyl dicarbonate

Tert-butyl 4-((R,E)-4-(methoxycarbonyl)but-3-en-2-yl)-1H-indole-1-carboxylate

Isopropenyl acetate

Downstream raw materials:

tert-butyl 4-hydroxyoctahydro-1H-indole-1-carboxylate

octahydropyrrolo[3,2-b]azepin-5(1H)one

tert-butyl 4-oxooctahydro-1H-indole-1-carboxylate

(-)-(3aR,4S,7aR)-4-hydroxy-4-(m-tolylethynyl)-octahydro-indole-1-carboxylic acid tert-butyl ester