(2S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,3-dihydro-1H-indole

Base Information

• Chemical Name: (2S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,3-dihydro-1H-indole
• CAS No.: 321744-15-4
• Molecular Formula: C₁₅H₂₅NOSi
• Molecular Weight: 263.455
• Mol file: 321744-15-4.mol

Synonyms:(2S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,3-dihydro-1H-indole

Chemical Property of (2S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,3-dihydro-1H-indole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,3-dihydro-1H-indole

There total 3 articles about (2S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,3-dihydro-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:

2-isopropyl-4-nitrobenzenesulfonyl chloride + (±)-2-(((tert-butyldimethylsilyl)oxy)methyl)indoline (321744-15-4) → (2S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,3-dihydro-1H-indole (321744-15-4) + (R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-1-((2-ethyl-4-nitrophenyl)sulfonyl)indoline + 2-(((tert-butyldimethylsilyl)oxy)methyl)-1-((2-ethyl-4-nitrophenyl)sulfonyl)indoline

Guidance literature:

With 4-(dimethylamino)-2-(5’-phenyl-3,5-bis(trifluoromethyl)-[1,1':3',1''-terphenyl]-2-yl)pyridine-N-oxide; N-ethyl-N,N-diisopropylamine; In toluene; at -78 ℃; for 5h; enantioselective reaction; Inert atmosphere;

DOI:10.1002/anie.201700977

Reference yield:

2,3-Dihydro-1H-indol-2-ylmethanol (27640-31-9,27640-33-1,77122-21-5,138969-57-0) → (2S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,3-dihydro-1H-indole (321744-15-4) + (R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-1-((2-ethyl-4-nitrophenyl)sulfonyl)indoline

Guidance literature:

Multi-step reaction with 2 steps

1: 1-methyl-1H-imidazole; N-ethyl-N,N-diisopropylamine / dichloromethane / 21.5 h / 20 °C / Inert atmosphere

2: 4-(dimethylamino)-2-(5’-phenyl-3,5-bis(trifluoromethyl)-[1,1':3',1''-terphenyl]-2-yl)pyridine-N-oxide; N-ethyl-N,N-diisopropylamine / toluene / 5 h / -78 °C / Inert atmosphere

With 1-methyl-1H-imidazole; 4-(dimethylamino)-2-(5’-phenyl-3,5-bis(trifluoromethyl)-[1,1':3',1''-terphenyl]-2-yl)pyridine-N-oxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; toluene;

DOI:10.1002/anie.201700977

Reference yield:

indolin-2-yl carboxylic acid (16851-56-2,78348-24-0) → (2S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,3-dihydro-1H-indole (321744-15-4) + (R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-1-((2-ethyl-4-nitrophenyl)sulfonyl)indoline

Guidance literature:

Multi-step reaction with 3 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere

2: 1-methyl-1H-imidazole; N-ethyl-N,N-diisopropylamine / dichloromethane / 21.5 h / 20 °C / Inert atmosphere

3: 4-(dimethylamino)-2-(5’-phenyl-3,5-bis(trifluoromethyl)-[1,1':3',1''-terphenyl]-2-yl)pyridine-N-oxide; N-ethyl-N,N-diisopropylamine / toluene / 5 h / -78 °C / Inert atmosphere

With 1-methyl-1H-imidazole; lithium aluminium tetrahydride; 4-(dimethylamino)-2-(5’-phenyl-3,5-bis(trifluoromethyl)-[1,1':3',1''-terphenyl]-2-yl)pyridine-N-oxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1002/anie.201700977

upstream raw materials:

2,3-Dihydro-1H-indol-2-ylmethanol

indolin-2-yl carboxylic acid

Downstream raw materials:

2-Benzenesulfonyl-1-[2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-indol-1-yl]-ethanone

(2S)-2,3-dihydro-1H-indole-2-ylmethanol

1,2-dihydro-3H-pyrrolo<1,2-a>indol-3-one

2-Benzenesulfonyl-1-[2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-indol-1-yl]-2-diazo-ethanone