tert-butyl 2-(hydroxydimethylsilyl)-5-methyl-1H-indole-1-carboxylate

Base Information

• Chemical Name: tert-butyl 2-(hydroxydimethylsilyl)-5-methyl-1H-indole-1-carboxylate
• CAS No.: 475102-18-2
• Molecular Formula: C16H23NO3Si
• Molecular Weight: 305.449
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID90452771
• Nikkaji Number: J1.814.451D
• Wikidata: Q82273591
• Mol file: 475102-18-2.mol

Synonyms:475102-18-2;tert-butyl 2-(hydroxydimethylsilyl)-5-methyl-1H-indole-1-carboxylate;1-BOC-2-(HYDROXY-DIMETHYL-SILANYL)-5-METHYL-INDOLE;tert-butyl 2-[hydroxy(dimethyl)silyl]-5-methylindole-1-carboxylate;C16H23NO3Si;S-3-amino-3-phenylpropan-1-ol;DTXSID90452771;SB37290;tert-butyl2-(hydroxydimethylsilyl)-5-methyl-1H-indole-1-carboxylate;5-Methyl-2-(hydroxydimethylsilyl)-1H-indole-1-carboxylic acid tert-butyl ester

Chemical Property of tert-butyl 2-(hydroxydimethylsilyl)-5-methyl-1H-indole-1-carboxylate

Chemical Property:

• PSA: 51.46000
• LogP: 3.13730
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 305.14472013
• Heavy Atom Count: 21
• Complexity: 405

Purity/Quality:

98% ^*data from raw suppliers

tert-Butyl2-(hydroxydimethylsilyl)-5-methyl-1H-indole-1-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C=C1)N(C(=C2)[Si](C)(C)O)C(=O)OC(C)(C)C

Technology Process of tert-butyl 2-(hydroxydimethylsilyl)-5-methyl-1H-indole-1-carboxylate

There total 3 articles about tert-butyl 2-(hydroxydimethylsilyl)-5-methyl-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: 91.0%

5-methylindole-1-carboxylic acid tert-butyl ester (129822-49-7) + dimethylsilicon dichloride (75-78-5,30107-43-8) → 2-(hydroxydimethylsilyl)-5-methyl-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester (475102-18-2)

Guidance literature:

5-methylindole-1-carboxylic acid tert-butyl ester; dimethylsilicon dichloride; With lithium diisopropyl amide; In tetrahydrofuran; at 0 - 5 ℃; for 0.5h;

With sodium hydrogencarbonate; for 1h; Further stages.;

DOI:10.1021/jo026087j

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 2-(hydroxydimethylsilyl)-5-methyl-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester (475102-18-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: DMAP / CH₂Cl₂ / 0.75 h / 20 °C

2.1: LDA / tetrahydrofuran / 0.5 h / 0 - 5 °C

2.2: 91 percent / aq. NaHCO₃ / 1 h

With dmap; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo026087j

Reference yield:

5-methyl-1H-indole (614-96-0) → 2-(hydroxydimethylsilyl)-5-methyl-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester (475102-18-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: DMAP / CH₂Cl₂ / 0.75 h / 20 °C

2.1: LDA / tetrahydrofuran / 0.5 h / 0 - 5 °C

2.2: 91 percent / aq. NaHCO₃ / 1 h

With dmap; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo026087j

upstream raw materials:

5-methylindole-1-carboxylic acid tert-butyl ester

dimethylsilicon dichloride

di-tert-butyl dicarbonate

5-methyl-1H-indole