(3S)-(E)-N-methoxycarbonyl-N-[2-[2-(3-tert-butyldimethylsilyloxy-1-butenyl)phenyl]ethyl]amine

Base Information

• Chemical Name: (3S)-(E)-N-methoxycarbonyl-N-[2-[2-(3-tert-butyldimethylsilyloxy-1-butenyl)phenyl]ethyl]amine
• CAS No.: 1273546-94-3
• Molecular Formula: C₂₀H₃₃NO₃Si
• Molecular Weight: 363.572
• Mol file: 1273546-94-3.mol

Synonyms:(3S)-(E)-N-methoxycarbonyl-N-[2-[2-(3-tert-butyldimethylsilyloxy-1-butenyl)phenyl]ethyl]amine

Chemical Property of (3S)-(E)-N-methoxycarbonyl-N-[2-[2-(3-tert-butyldimethylsilyloxy-1-butenyl)phenyl]ethyl]amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S)-(E)-N-methoxycarbonyl-N-[2-[2-(3-tert-butyldimethylsilyloxy-1-butenyl)phenyl]ethyl]amine

There total 3 articles about (3S)-(E)-N-methoxycarbonyl-N-[2-[2-(3-tert-butyldimethylsilyloxy-1-butenyl)phenyl]ethyl]amine 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: 84.0%

methyl 2-(2-bromophenyl)ethylcarbamate (1109230-24-1) + (S,E)-tert-butyldimethyl((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-yl)oxy)silane (1198272-03-5) → (3S)-(E)-N-methoxycarbonyl-N-[2-[2-(3-tert-butyldimethylsilyloxy-1-butenyl)phenyl]ethyl]amine (1273546-94-3)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydrogencarbonate; In 1,4-dioxane; water; at 80 ℃; for 2h;

DOI:10.1021/jo102452d

Reference yield:

2-(2-bromophenyl)acetonitrile (19472-74-3) → (3S)-(E)-N-methoxycarbonyl-N-[2-[2-(3-tert-butyldimethylsilyloxy-1-butenyl)phenyl]ethyl]amine (1273546-94-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium tetrahydroborate; nickel(II) chloride hexahydrate / methanol / 1.5 h / 0 - 20 °C

1.2: 0.5 h

2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydrogencarbonate / 1,4-dioxane; water / 2 h / 80 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; nickel(II) chloride hexahydrate; sodium hydrogencarbonate; In 1,4-dioxane; methanol; water; 2.1: Suzuki coupling;

DOI:10.1021/jo102452d

Reference yield:

(S)-3-(tert-butyldimethylsilyloxy)but-1-yne (150406-34-1) → (3S)-(E)-N-methoxycarbonyl-N-[2-[2-(3-tert-butyldimethylsilyloxy-1-butenyl)phenyl]ethyl]amine (1273546-94-3)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 24 h / 130 °C / Sealed tube

2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydrogencarbonate / 1,4-dioxane; water / 2 h / 80 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydrogencarbonate; In tetrahydrofuran; 1,4-dioxane; water; 2: Suzuki coupling;

DOI:10.1021/jo102452d

upstream raw materials:

methyl 2-(2-bromophenyl)ethylcarbamate

(S,E)-tert-butyldimethyl((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-yl)oxy)silane

2-(2-bromophenyl)acetonitrile

(S)-3-(tert-butyldimethylsilyloxy)but-1-yne

Downstream raw materials:

(3S)-(E)-N-methoxycarbonyl-N-[2-[2-(3-hydroxy-1-butenyl)phenyl]ethyl]amine