methyl (2S,3R,αS)-2-methyl-3-[N-benzyl-N-(α-methylbenzyl)amino]-4-(N'-benzyl-N'-allylamino)butanoate

Base Information

• Chemical Name: methyl (2S,3R,αS)-2-methyl-3-[N-benzyl-N-(α-methylbenzyl)amino]-4-(N'-benzyl-N'-allylamino)butanoate
• CAS No.: 945483-37-4
• Molecular Formula: C₃₁H₃₈N₂O₂
• Molecular Weight: 470.655
• Mol file: 945483-37-4.mol

Synonyms:methyl (2S,3R,αS)-2-methyl-3-[N-benzyl-N-(α-methylbenzyl)amino]-4-(N'-benzyl-N'-allylamino)butanoate

Chemical Property of methyl (2S,3R,αS)-2-methyl-3-[N-benzyl-N-(α-methylbenzyl)amino]-4-(N'-benzyl-N'-allylamino)butanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2S,3R,αS)-2-methyl-3-[N-benzyl-N-(α-methylbenzyl)amino]-4-(N'-benzyl-N'-allylamino)butanoate

There total 6 articles about methyl (2S,3R,αS)-2-methyl-3-[N-benzyl-N-(α-methylbenzyl)amino]-4-(N'-benzyl-N'-allylamino)butanoate 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: 83.0%

methyl (E)-(N-allyl-N-benzylamino)but-2-enoate (945483-25-0) + (S)-N-benzyl-1-phenylethylamine (17480-69-2) + methyl iodide (74-88-4) → methyl (2S,3R,αS)-2-methyl-3-[N-benzyl-N-(α-methylbenzyl)amino]-4-(N'-benzyl-N'-allylamino)butanoate (945483-37-4) + C31H38N2O2

Guidance literature:

methyl (E)-(N-allyl-N-benzylamino)but-2-enoate; (S)-N-benzyl-1-phenylethylamine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 2h;

methyl iodide; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 16h; Further stages.;

DOI:10.1039/b704932c

Reference yield:

methyl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4-(N'-benzyl-N'-allylamino)butanoate (906750-02-5) + methyl iodide (74-88-4) → methyl (2S,3R,αS)-2-methyl-3-[N-benzyl-N-(α-methylbenzyl)amino]-4-(N'-benzyl-N'-allylamino)butanoate (945483-37-4) + C31H38N2O2

Guidance literature:

methyl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4-(N'-benzyl-N'-allylamino)butanoate; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 2h;

methyl iodide; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 16h; Further stages. Title compound not separated from byproducts.;

DOI:10.1039/b704932c

Reference yield:

Allylbenzylamine (4383-22-6) → methyl (2S,3R,αS)-2-methyl-3-[N-benzyl-N-(α-methylbenzyl)amino]-4-(N'-benzyl-N'-allylamino)butanoate (945483-37-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 100 percent / iPr₂NEt / CH₂Cl₂ / 16 h / 0 °C

2.1: 15.0 g / BuLi / hexane; tetrahydrofuran / 2 h / -78 °C

3.1: LDA / hexane; tetrahydrofuran / 2 h / -78 °C

3.2: tetrahydrofuran; hexane / 16 h / -78 - 20 °C

With n-butyllithium; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1039/b704932c

upstream raw materials:

methyl (E)-(N-allyl-N-benzylamino)but-2-enoate

(S)-N-benzyl-1-phenylethylamine

methyl iodide

methyl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4-(N'-benzyl-N'-allylamino)butanoate

Downstream raw materials:

(3R,4R,αS)-N(1)-benzyl-3-[N'-benzyl-N'-(α-methylbenzyl)amino]-4-methylpyrrolidine

(3S,4R,αS)-N(1)-benzyl-3-methyl-4-[N'-benzyl-N'-(α-methylbenzyl)amino]pyrrolid-2-one