N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-4-methyl-N-(3-oxo-3-pyrrolidin-1-yl-propyl)-benzenesulfonamide

Base Information

• Chemical Name: N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-4-methyl-N-(3-oxo-3-pyrrolidin-1-yl-propyl)-benzenesulfonamide
• CAS No.: 300363-45-5
• Molecular Formula: C₃₄H₄₄N₂O₄SSi
• Molecular Weight: 604.886
• Mol file: 300363-45-5.mol

Synonyms:N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-4-methyl-N-(3-oxo-3-pyrrolidin-1-yl-propyl)-benzenesulfonamide

Chemical Property of N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-4-methyl-N-(3-oxo-3-pyrrolidin-1-yl-propyl)-benzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-4-methyl-N-(3-oxo-3-pyrrolidin-1-yl-propyl)-benzenesulfonamide

There total 5 articles about N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-4-methyl-N-(3-oxo-3-pyrrolidin-1-yl-propyl)-benzenesulfonamide 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: 80.0%

pyrrolidine (123-75-1) + 3-[[1-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-(toluene-4-sulfonyl)-amino]-propionic acid (300363-44-4) → N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-4-methyl-N-(3-oxo-3-pyrrolidin-1-yl-propyl)-benzenesulfonamide (300363-45-5)

Guidance literature:

With dmap; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; In dichloromethane;

DOI:10.1016/S0957-4166(00)00237-8

Reference yield:

[(1R)-1-({[(1,1-dimethylethyl)(diphenyl)silyl]oxy}methyl)-2-propen-1-yl]amine → N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-4-methyl-N-(3-oxo-3-pyrrolidin-1-yl-propyl)-benzenesulfonamide (300363-45-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / methanol

2: 98 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

3: 86 percent / aq. LiOH / acetone

4: 80 percent / BOPCl; DMAP / CH₂Cl₂

With dmap; lithium hydroxide; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; In methanol; dichloromethane; acetone; 1: Michael addition / 2: Tosylation / 3: Hydrolysis / 4: Acylation;

DOI:10.1016/S0957-4166(00)00237-8

Reference yield:

(+)-1,1-dimethylethyl [(1R)-1-({[(1,1-dimethylethyl)(diphenyl)silyl]oxy}methyl)prop-2-en-1-yl]carbamate (300363-41-1) → N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-4-methyl-N-(3-oxo-3-pyrrolidin-1-yl-propyl)-benzenesulfonamide (300363-45-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / TBDMSTf; 2,6-lutidine / CH₂Cl₂ / 20 h / 20 °C

2: 94 percent / methanol

3: 98 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

4: 86 percent / aq. LiOH / acetone

5: 80 percent / BOPCl; DMAP / CH₂Cl₂

With 2,6-dimethylpyridine; dmap; lithium hydroxide; t-butyldimethylsiyl triflate; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; In methanol; dichloromethane; acetone; 1: Ohfune deacylation / 2: Michael addition / 3: Tosylation / 4: Hydrolysis / 5: Acylation;

DOI:10.1016/S0957-4166(00)00237-8

upstream raw materials:

pyrrolidine

3-[[1-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-(toluene-4-sulfonyl)-amino]-propionic acid

(+)-1,1-dimethylethyl [(1R)-1-({[(1,1-dimethylethyl)(diphenyl)silyl]oxy}methyl)prop-2-en-1-yl]carbamate

3-[1-(tert-butyl-diphenyl-silanyloxymethyl)-allylamino]-propionic acid methyl ester

Downstream raw materials:

N-(1-benzyloxymethyl-allyl)-4-methyl-N-(3-oxo-3-pyrrolidin-1-yl-propyl)-benzenesulfonamide

N-(1-hydroxymethyl-allyl)-4-methyl-N-(3-oxo-3-pyrrolidin-1-yl-propyl)-benzenesulfonamide