(+/-)-2,3-Dihydro-6-hydroxy-3-(((methylsulfonyl)oxy)methyl)-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester

Base Information

Chemical Name:(+/-)-2,3-Dihydro-6-hydroxy-3-(((methylsulfonyl)oxy)methyl)-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester
CAS No.:119880-05-6
Molecular Formula:C₁₅H₂₁NO₆S
Molecular Weight:343.401
Hs Code.:
NSC Number:676515
DSSTox Substance ID:DTXSID30923132
ChEMBL ID:CHEMBL1964795

Synonyms:119880-05-6;CHEMBL1964795;DTXSID30923132;NSC676515;NSC-676515;(+/-)-2,3-Dihydro-6-hydroxy-3-(((methylsulfonyl)oxy)methyl)-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester;NCI60_027081;1-[(t-Butyloxy)carbonyl]-6-hydroxy-3-{[(methanesulfonyl)-oxy]methyl}indoline;tert-Butyl 6-hydroxy-3-{[(methanesulfonyl)oxy]methyl}-2,3-dihydro-1H-indole-1-carboxylate

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Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (+/-)-2,3-Dihydro-6-hydroxy-3-(((methylsulfonyl)oxy)methyl)-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester

Chemical Property:

Vapor Pressure:2.34E-11mmHg at 25°C
Boiling Point:518.2°Cat760mmHg
Flash Point:267.2°C
Density:1.319g/cm³
XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:5
Exact Mass:343.10895856
Heavy Atom Count:23
Complexity:535

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC(C)(C)OC(=O)N1CC(C2=C1C=C(C=C2)O)COS(=O)(=O)C

Technology Process of (+/-)-2,3-Dihydro-6-hydroxy-3-(((methylsulfonyl)oxy)methyl)-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester

There total 8 articles about (+/-)-2,3-Dihydro-6-hydroxy-3-(((methylsulfonyl)oxy)methyl)-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester 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: 75.0%

: 119880-03-4
6-(benzyloxy)-1-((tert-butyloxy)carbonyl)-3-(((methanesulfonyl)oxy)methyl)indoline

: 119880-05-6
1-((tert-butyloxy)carbonyl)-6-hydroxy-3-(((methanesulfonyl)oxy)methyl)indoline

Guidance literature:: With hydrogen; palladium on activated charcoal; In tetrahydrofuran; for 7h; under 760 Torr; Ambient temperature;

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 119880-05-6
1-((tert-butyloxy)carbonyl)-6-hydroxy-3-(((methanesulfonyl)oxy)methyl)indoline

Guidance literature:: Multi-step reaction with 6 steps

1: 85 percent / dioxane / 10 h / 105 °C

2: 68 percent / NaH / tetrahydrofuran; dimethylformamide / 3 h / 25 °C

3: 91 percent / Bu₃SnH, AIBN / benzene / 3 h / 80 °C

4: 1.) ozone, 2.) NaBH₄ / 1.) EtOH, -78 deg C, 3 min, 2.) EtOH, H₂O, -78 to 24 deg C, 4 h

5: 89 percent / Et₃N / CH₂Cl₂ / 0.42 h / 0 °C

6: 75 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 7 h / 24 °C / 760 Torr

With sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; sodium hydride; ozone; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00267a004

Reference yield:

: 1484-26-0
3-(benzyloxy)aniline

: 119880-05-6
1-((tert-butyloxy)carbonyl)-6-hydroxy-3-(((methanesulfonyl)oxy)methyl)indoline

Guidance literature:: Multi-step reaction with 7 steps

1: 42 percent / N-bromosuccinimide, H₂SO₄ / tetrahydrofuran / 10 h / -78 °C

2: 85 percent / dioxane / 10 h / 105 °C

3: 68 percent / NaH / tetrahydrofuran; dimethylformamide / 3 h / 25 °C

4: 91 percent / Bu₃SnH, AIBN / benzene / 3 h / 80 °C

5: 1.) ozone, 2.) NaBH₄ / 1.) EtOH, -78 deg C, 3 min, 2.) EtOH, H₂O, -78 to 24 deg C, 4 h

6: 89 percent / Et₃N / CH₂Cl₂ / 0.42 h / 0 °C

7: 75 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 7 h / 24 °C / 760 Torr

With sodium tetrahydroborate; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); sulfuric acid; hydrogen; tri-n-butyl-tin hydride; sodium hydride; ozone; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00267a004