(1R)-N-(tert-butyloxycarbonyl)-1-(N-tosyl-6-bromoindol-3-yl)-2-[(4-methylphenylsulfonyl)oxy]ethylamine

Base Information

Chemical Name:(1R)-N-(tert-butyloxycarbonyl)-1-(N-tosyl-6-bromoindol-3-yl)-2-[(4-methylphenylsulfonyl)oxy]ethylamine
CAS No.:354538-35-5
Molecular Formula:C₂₉H₃₁BrN₂O₇S₂
Molecular Weight:663.61
Hs Code.:

Synonyms:(1R)-N-(tert-butyloxycarbonyl)-1-(N-tosyl-6-bromoindol-3-yl)-2-[(4-methylphenylsulfonyl)oxy]ethylamine

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Chemical Property of (1R)-N-(tert-butyloxycarbonyl)-1-(N-tosyl-6-bromoindol-3-yl)-2-[(4-methylphenylsulfonyl)oxy]ethylamine

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Technology Process of (1R)-N-(tert-butyloxycarbonyl)-1-(N-tosyl-6-bromoindol-3-yl)-2-[(4-methylphenylsulfonyl)oxy]ethylamine

There total 17 articles about (1R)-N-(tert-butyloxycarbonyl)-1-(N-tosyl-6-bromoindol-3-yl)-2-[(4-methylphenylsulfonyl)oxy]ethylamine 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%

: 936824-50-9
tert-butyl (R)-{1-(6'-bromoindol-3'-yl)-2-hydroxy}ethylcarbamate

: 98-59-9
p-toluenesulfonyl chloride

: 354538-35-5
(1R)-N-(tert-butyloxycarbonyl)-1-(N-tosyl-6-bromoindol-3-yl)-2-[(4-methylphenylsulfonyl)oxy]ethylamine

Guidance literature:: With dmap; triethylamine; In dichloromethane; at -20 ℃; for 20h;
DOI:10.1055/s-2007-965907

Reference yield:

: 98-59-9
p-toluenesulfonyl chloride

: 1,1-dimethylethyl (1R)-N-[1-[6-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl]-2-hydroxy]ethylcarbamate

: 354538-35-5
(1R)-N-(tert-butyloxycarbonyl)-1-(N-tosyl-6-bromoindol-3-yl)-2-[(4-methylphenylsulfonyl)oxy]ethylamine

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 5h;
DOI:10.1021/jo010265b

Reference yield:

: 17826-04-9
6-bromo-1H-indole-3-carbaldehyde

: 354538-35-5
(1R)-N-(tert-butyloxycarbonyl)-1-(N-tosyl-6-bromoindol-3-yl)-2-[(4-methylphenylsulfonyl)oxy]ethylamine

Guidance literature:: Multi-step reaction with 9 steps

1.1: 100 percent / K₂CO₃ / butan-2-one / 3 h / Heating

2.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C

2.2: 90 percent / tetrahydrofuran / 0.33 h / 0 °C

3.1: 92 percent / AD-mix-α / H2O; 2-methyl-propan-2-ol / 13 h / 0 - 20 °C

4.1: 94 percent / imidazole / CH₂Cl₂ / 12.5 h / 0 - 20 °C

5.1: 87 percent / Ph₃P; diethyl azodicarboxylate; diphenylphosphoryl azide / tetrahydrofuran; toluene / -20 - 20 °C

6.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

7.1: LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

8.1: Et₃N / CH₂Cl₂ / 4 h / 0 °C

9.1: 335 mg / Et₃N; DMAP / CH₂Cl₂ / 5 h / 20 °C

With 1H-imidazole; dmap; AD-mix-α; lithium aluminium tetrahydride; n-butyllithium; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; potassium carbonate; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; hexane; dichloromethane; water; toluene; butanone; tert-butyl alcohol; 2.2: Wittig olefination / 3.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/jo010265b