Propanedioic acid, [5-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-2-pyrrolidinylidene]-, bis(phenylmethyl) ester, (R)-

Base Information

• Chemical Name: Propanedioic acid, [5-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-2-pyrrolidinylidene]-, bis(phenylmethyl) ester, (R)-
• CAS No.: 142890-18-4
• Molecular Formula: C38H41NO5Si
• Molecular Weight: 619.833
• Mol file: 142890-18-4.mol

Synonyms:

Chemical Property of Propanedioic acid, [5-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-2-pyrrolidinylidene]-, bis(phenylmethyl) ester, (R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Propanedioic acid, [5-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-2-pyrrolidinylidene]-, bis(phenylmethyl) ester, (R)-

There total 4 articles about Propanedioic acid, [5-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-2-pyrrolidinylidene]-, bis(phenylmethyl) ester, (R)- 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: 99.0%

dibenzyl 2-bromomalonate (65100-24-5) + (R)-5-(tert-butyldiphenylsiloxy)methylpyrrolidin-2-thione (142890-14-0) → (R)-2-[5-(tert-butyldiphenylsiloxy)methylpyrrolidin-2-ylidene]malonic acid dibenzyl ester (142890-18-4)

Guidance literature:

dibenzyl 2-bromomalonate; (R)-5-(tert-butyldiphenylsiloxy)methylpyrrolidin-2-thione; In dichloromethane; at 20 ℃; for 12h;

With potassium hydrogencarbonate; In dichloromethane; water; at 20 ℃; for 4h;

DOI:10.1016/S0040-4020(03)00377-6

Reference yield:

(R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-2-one (138629-44-4) → (R)-2-[5-(tert-butyldiphenylsiloxy)methylpyrrolidin-2-ylidene]malonic acid dibenzyl ester (142890-18-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 96 percent / Lawesson's reagent / toluene / 0.33 h / Heating

2.1: CH₂Cl₂ / 12 h / 20 °C

2.2: 99 percent / KHCO₃ / H₂O; CH₂Cl₂ / 4 h / 20 °C

With Lawessons reagent; In dichloromethane; toluene; 2.1: Eschenmoser sulfide contraction;

DOI:10.1016/S0040-4020(03)00377-6

Reference yield:

(R)-5-hydroxymethylpyrrolidin-2-one (66673-40-3) → (R)-2-[5-(tert-butyldiphenylsiloxy)methylpyrrolidin-2-ylidene]malonic acid dibenzyl ester (142890-18-4)

Guidance literature:

Multi-step reaction with 3 steps

1: imidazole (ImH) / dimethylformamide / 12 h / Ambient temperature

2: Lawesson's regent / toluene / 0.33 h / Heating

3: 2.) aq. KHCO₃ / 1.) CH₂Cl₂, RT, 2 h, 2.) CH₂Cl₂, 4 h

With Lawessons reagent; 1H-imidazole; potassium hydrogencarbonate; In N,N-dimethyl-formamide; toluene;

DOI:10.1246/cl.1992.975

upstream raw materials:

dibenzyl 2-bromomalonate

(R)-5-(tert-butyldiphenylsiloxy)methylpyrrolidin-2-thione

(R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-2-one

(R)-5-hydroxymethylpyrrolidin-2-one

Downstream raw materials:

(R)-2-(5-hydroxymethylpyrrolidin-2-ylidene)malonic acid dibenzyl ester

(R)-2-(1-azabicyclo[3.1.0]hex-2-ylidene)malonic acid dibenzyl ester

(R)-2-(5-bromomethylpyrrolidin-2-ylidene)malonic acid dibenzyl ester

(R)-2-(5-iodomethylpyrrolidin-2-ylidene)malonic acid dibenzyl ester