2-[(allyl-benzyl-amino)-methyl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enoic acid methyl ester

Base Information

• Chemical Name: 2-[(allyl-benzyl-amino)-methyl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enoic acid methyl ester
• CAS No.: 881398-70-5
• Molecular Formula: C₂₄H₃₉NO₃Si
• Molecular Weight: 417.664
• Mol file: 881398-70-5.mol

Synonyms:2-[(allyl-benzyl-amino)-methyl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enoic acid methyl ester

Chemical Property of 2-[(allyl-benzyl-amino)-methyl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(allyl-benzyl-amino)-methyl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enoic acid methyl ester

There total 5 articles about 2-[(allyl-benzyl-amino)-methyl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enoic acid methyl ester 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: 70.0%

((2-(bromomethyl)allyl)oxy)(tert-butyl)dimethylsilane (211859-87-9) + 3-(allyl-benzyl-amino)-propionic acid methyl ester (473914-75-9) → 2-[(allyl-benzyl-amino)-methyl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enoic acid methyl ester (881398-70-5)

Guidance literature:

3-(allyl-benzyl-amino)-propionic acid methyl ester; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

((2-(bromomethyl)allyl)oxy)(tert-butyl)dimethylsilane; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; hexane; at -78 - -40 ℃;

DOI:10.1016/j.tet.2005.11.049

Reference yield:

3-allylamino-propionic acid methyl ester (37732-74-4) → 2-[(allyl-benzyl-amino)-methyl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enoic acid methyl ester (881398-70-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 89 percent / K₂CO₃ / acetonitrile / 3 h / Heating

2.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 70 percent / HMPT / tetrahydrofuran; hexane / -78 - -40 °C

With potassium carbonate; lithium diisopropyl amide; In tetrahydrofuran; hexane; acetonitrile;

DOI:10.1016/j.tet.2005.11.049

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 2-[(allyl-benzyl-amino)-methyl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enoic acid methyl ester (881398-70-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 91 percent / TEA; DMAP / CH₂Cl₂ / 0 - 20 °C

2.1: 80 percent / DIBAL-H / tetrahydrofuran; toluene / -78 - 0 °C

3.1: 84 percent / bromine; triphenylphosphine; imidazole / CH₂Cl₂ / 0.5 h / 0 °C

4.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

4.2: 70 percent / HMPT / tetrahydrofuran; hexane / -78 - -40 °C

With 1H-imidazole; dmap; TEA; bromine; diisobutylaluminium hydride; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; toluene;

DOI:10.1016/j.tet.2005.11.049

upstream raw materials:

((2-(bromomethyl)allyl)oxy)(tert-butyl)dimethylsilane

3-(allyl-benzyl-amino)-propionic acid methyl ester

3-allylamino-propionic acid methyl ester

tert-butyldimethylsilyl chloride