2-(((tert-butyl)diphenylsilanyloxy)ethyl)-5-methyl-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridine

Base Information

• Chemical Name: 2-(((tert-butyl)diphenylsilanyloxy)ethyl)-5-methyl-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridine
• CAS No.: 1334404-46-4
• Molecular Formula: C₃₁H₃₉NO₃SSi
• Molecular Weight: 533.807
• Mol file: 1334404-46-4.mol

Synonyms:2-(((tert-butyl)diphenylsilanyloxy)ethyl)-5-methyl-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridine

Chemical Property of 2-(((tert-butyl)diphenylsilanyloxy)ethyl)-5-methyl-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(((tert-butyl)diphenylsilanyloxy)ethyl)-5-methyl-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridine

There total 7 articles about 2-(((tert-butyl)diphenylsilanyloxy)ethyl)-5-methyl-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridine 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-(((tert-butyl)diphenylsilanoxy)ethyl)-5-methylene-1-(toluene-4-sulfonyl)piperidine (1334404-42-0) → 2-(((tert-butyl)diphenylsilanyloxy)ethyl)-5-methyl-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydropyridine (1334404-47-5) + 2-(((tert-butyl)diphenylsilanyloxy)ethyl)-5-methyl-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridine (1334404-46-4)

Guidance literature:

With Wilkinson's catalyst; 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; at 40 ℃; for 16h; Molecular sieve;

DOI:10.1039/c1cc13048j

Reference yield:

N-(3-hydroxy-1-hydroxymethylpropyl)-4-methylbenzenesulfonamide → 2-(((tert-butyl)diphenylsilanyloxy)ethyl)-5-methyl-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydropyridine (1334404-47-5) + 2-(((tert-butyl)diphenylsilanyloxy)ethyl)-5-methyl-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridine (1334404-46-4)

Guidance literature:

Multi-step reaction with 5 steps

1: tributylphosphine; 1,1'-azodicarbonyl-dipiperidine / toluene / 0 - 20 °C

2: 1H-imidazole / tetrahydrofuran / 0 - 20 °C

3: tetrahydrofuran / 16 h / 20 °C

4: palladium diacetate; triphenylphosphine / toluene / 16 h / Molecular sieve; Reflux

5: Wilkinson's catalyst; 1,8-diazabicyclo[5.4.0]undec-7-ene / ethanol / 16 h / 40 °C / Molecular sieve

With 1H-imidazole; Wilkinson's catalyst; tributylphosphine; palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; ethanol; toluene; 1: Mitsunobu reaction;

DOI:10.1039/c1cc13048j

Reference yield:

(R)-2-(((tert-butyl)diphenylsilanoxy)ethyl)-1-(toluene-4-sulfonyl)aziridine → 2-(((tert-butyl)diphenylsilanyloxy)ethyl)-5-methyl-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydropyridine (1334404-47-5) + 2-(((tert-butyl)diphenylsilanyloxy)ethyl)-5-methyl-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridine (1334404-46-4)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran / 16 h / 20 °C

2: palladium diacetate; triphenylphosphine / toluene / 16 h / Molecular sieve; Reflux

3: Wilkinson's catalyst; 1,8-diazabicyclo[5.4.0]undec-7-ene / ethanol / 16 h / 40 °C / Molecular sieve

With Wilkinson's catalyst; palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; In tetrahydrofuran; ethanol; toluene;

DOI:10.1039/c1cc13048j

upstream raw materials:

2-hydroxyethyl-1-(toluene-4-sulfonyl)aziridine

C₃₁H₄₁NO₄SSi

2-(((tert-butyl)diphenylsilanoxy)ethyl)-5-methylene-1-(toluene-4-sulfonyl)piperidine

p-toluenesulfonyl chloride

Downstream raw materials:

8-bromo-8-methyl-9-(toluene-4-sulfonyl)-2-oxa-9-azabicyclo[3.3.1]nonane