2-Azaspiro[4.4]non-7-ene, 3-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-2-[(4-methylphenyl)sulfon yl]-, (3S)-

Base Information

• Chemical Name: 2-Azaspiro[4.4]non-7-ene, 3-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-2-[(4-methylphenyl)sulfon yl]-, (3S)-
• CAS No.: 569656-64-0
• Molecular Formula: C32H39NO3SSi
• Molecular Weight: 545.818
• Mol file: 569656-64-0.mol

Synonyms:

Chemical Property of 2-Azaspiro[4.4]non-7-ene, 3-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-2-[(4-methylphenyl)sulfon yl]-, (3S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Azaspiro[4.4]non-7-ene, 3-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-2-[(4-methylphenyl)sulfon yl]-, (3S)-

There total 9 articles about 2-Azaspiro[4.4]non-7-ene, 3-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-2-[(4-methylphenyl)sulfon yl]-, (3S)- 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: 96.0%

(2S)(2-tert-butyldiphenylsilyloxymethyl)-4,4-diallyl-1-(toluene-4-sulfonyl)pyrrolidine (569656-63-9) → 3-(tert-butyl-diphenyl-silanyloxymethyl)-2-(toluene-4-sulfonyl)-2-aza-spiro[4.4]non-7-ene (569656-64-0)

Guidance literature:

Grubbs catalyst first generation; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1039/b300314k

Reference yield:

(2S,4R)-2-Hydroxymethyl-4-hydroxy-1-(4-toluenesulfonyl)-pyrrolidine (57850-05-2,93136-91-5,116143-08-9,132998-42-6,5605-46-9) → 3-(tert-butyl-diphenyl-silanyloxymethyl)-2-(toluene-4-sulfonyl)-2-aza-spiro[4.4]non-7-ene (569656-64-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 3.0 g / imidazole / dimethylformamide / 20 °C

2: 2.6 g / PDC; 4 Angstroeme molecular sieves / CH₂Cl₂ / 4 h / 20 °C

3: 4.18 g / benzene / 24 h / Heating

4: 3.6 g / DIBAL-H / toluene; CH₂Cl₂ / 0.75 h / -78 °C

5: 78 percent / Et₂Zn / CH₂Cl₂

6: CBr₄; PPh₃; Pyridine / CH₂Cl₂ / 0.5 h / 0 °C

7: AIBN / benzene / 8 h

8: 96 percent / Grubbs' catalyst / CH₂Cl₂ / 1.5 h / 20 °C

With pyridine; 1H-imidazole; dipyridinium dichromate; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; 4 A molecular sieve; diethylzinc; diisobutylaluminium hydride; triphenylphosphine; Grubbs catalyst first generation; In dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 3: Wittig reaction;

DOI:10.1039/b300314k

Reference yield:

(3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol (569656-76-4) → 3-(tert-butyl-diphenyl-silanyloxymethyl)-2-(toluene-4-sulfonyl)-2-aza-spiro[4.4]non-7-ene (569656-64-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 2.6 g / PDC; 4 Angstroeme molecular sieves / CH₂Cl₂ / 4 h / 20 °C

2: 4.18 g / benzene / 24 h / Heating

3: 3.6 g / DIBAL-H / toluene; CH₂Cl₂ / 0.75 h / -78 °C

4: 78 percent / Et₂Zn / CH₂Cl₂

5: CBr₄; PPh₃; Pyridine / CH₂Cl₂ / 0.5 h / 0 °C

6: AIBN / benzene / 8 h

7: 96 percent / Grubbs' catalyst / CH₂Cl₂ / 1.5 h / 20 °C

With pyridine; dipyridinium dichromate; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; 4 A molecular sieve; diethylzinc; diisobutylaluminium hydride; triphenylphosphine; Grubbs catalyst first generation; In dichloromethane; toluene; benzene; 2: Wittig reaction;

DOI:10.1039/b300314k

upstream raw materials:

(2S)(2-tert-butyldiphenylsilyloxymethyl)-4,4-diallyl-1-(toluene-4-sulfonyl)pyrrolidine

(2S,4R)-2-Hydroxymethyl-4-hydroxy-1-(4-toluenesulfonyl)-pyrrolidine

tert-butylchlorodiphenylsilane

(5S)-(5-tert-butyldiphenylsilyloxymethyl)-1-(toluene-4-sulfonyl)pyrrolidin-3-one

Downstream raw materials:

(2S)-[2-(toluene-4-sulfonyl)-2-azaspiro[4.4]non-7-en-3-yl]methanol

(2S)-[(2-toluene-4-sulfonyl)-2-azaspiro[4.4]nonan-3-yl]methanol