(2E)-N-benzyl-4-(tert-butyldimethylsiloxy)but-2-en-1-amine

Base Information

• Chemical Name: (2E)-N-benzyl-4-(tert-butyldimethylsiloxy)but-2-en-1-amine
• CAS No.: 1099751-95-7
• Molecular Formula: C₁₇H₂₉NOSi
• Molecular Weight: 291.509
• Mol file: 1099751-95-7.mol

Synonyms:(2E)-N-benzyl-4-(tert-butyldimethylsiloxy)but-2-en-1-amine

Chemical Property of (2E)-N-benzyl-4-(tert-butyldimethylsiloxy)but-2-en-1-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E)-N-benzyl-4-(tert-butyldimethylsiloxy)but-2-en-1-amine

There total 5 articles about (2E)-N-benzyl-4-(tert-butyldimethylsiloxy)but-2-en-1-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: 99.0%

N-benzyl-4-[tert-butyldimethylsilyloxy-(2E)-buten-1-yl]trifluoroacetamide → (2E)-N-benzyl-4-(tert-butyldimethylsiloxy)but-2-en-1-amine (1099751-95-7)

Guidance literature:

With water; potassium carbonate; In methanol;

DOI:10.1002/ejoc.201301659

Reference yield:

(2E)-4-(tert-butyldimethylsiloxy)but-2-enyl methyl carbonate (1099751-57-1) + benzylamine (100-46-9) → (2E)-N-benzyl-4-(tert-butyldimethylsiloxy)but-2-en-1-amine (1099751-95-7) + (+)-(2S)-N-benzyl-1-(tert-butyldimethylsiloxy)but-3-en-2-amine (1099751-78-6)

Guidance literature:

With O,O'-((S)-1,1'-binaphthyl-2,2'-diyl)-N,N'-di-(S,S)-(1-naphthalen-1-yl)-ethyl-phosphoramidite; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; triethylamine; In tetrahydrofuran; at 20 ℃; for 2h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1055/s-0028-1083158

Reference yield:

[(Z)-4-[(tert-butyldimethylsilyl)oxy]-2-buten-1-yl] ethyl carbonate (163976-62-3) → (2E)-N-benzyl-4-(tert-butyldimethylsiloxy)but-2-en-1-amine (1099751-95-7)

Guidance literature:

Multi-step reaction with 2 steps

1: bis(η3-allyl-μ-chloropalladium(II)); sodium hydride; triphenylphosphine / N,N-dimethyl-formamide / Inert atmosphere; Reflux

2: potassium carbonate / methanol; water

With bis(η3-allyl-μ-chloropalladium(II)); sodium hydride; potassium carbonate; triphenylphosphine; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201301659

upstream raw materials:

(2E)-4-(tert-butyldimethylsiloxy)but-2-enyl methyl carbonate

benzylamine

[(Z)-4-[(tert-butyldimethylsilyl)oxy]-2-buten-1-yl] ethyl carbonate

(Z)-4-(tert-butyldimethylsilyloxy)but-2-en-1-ol

Downstream raw materials:

N-(fluorenylmethoxycarbonyl)glycine-{N-benzyl-N-[4-tert-butyldimethylsilyloxy-(2E)-buten-1-yl]}amide

N-(trifluoroacetyl)glycine {N-benzyl-N-[4-tert-butyldimethylsilyloxy-(2E)-buten-1-yl]}amide

N-(trifluoroacetyl)glycine {N-benzyl-N-[4-hydroxy-(2E)-buten-1-yl]}amide

N-(tert-butyloxycarbonyl)glycine {N-benzyl-N-[4-hydroxy-(2E)-buten-1-yl]}amide