tert-butyl (2S,3R,1'S,αR)-2-(1'-hydroxy)benzyl-3-[N-methyl-N-(α-methylbenzyl)amino]butanoate

Base Information

• Chemical Name: tert-butyl (2S,3R,1'S,αR)-2-(1'-hydroxy)benzyl-3-[N-methyl-N-(α-methylbenzyl)amino]butanoate
• CAS No.: 946065-13-0
• Molecular Formula: C₂₄H₃₃NO₃
• Molecular Weight: 383.531

Synonyms:tert-butyl (2S,3R,1'S,αR)-2-(1'-hydroxy)benzyl-3-[N-methyl-N-(α-methylbenzyl)amino]butanoate

Chemical Property of tert-butyl (2S,3R,1'S,αR)-2-(1'-hydroxy)benzyl-3-[N-methyl-N-(α-methylbenzyl)amino]butanoate

Chemical Property:

Purity/Quality:

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Technology Process of tert-butyl (2S,3R,1'S,αR)-2-(1'-hydroxy)benzyl-3-[N-methyl-N-(α-methylbenzyl)amino]butanoate

There total 3 articles about tert-butyl (2S,3R,1'S,αR)-2-(1'-hydroxy)benzyl-3-[N-methyl-N-(α-methylbenzyl)amino]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: 24.0%

tert-butyl (3R,αR)-3-[N-methyl-N-(α-methylbenzyl)amino]butanoate (946065-00-5) + benzaldehyde (100-52-7) → tert-butyl (2S,3R,1'S,αR)-2-(1'-hydroxy)benzyl-3-[N-methyl-N-(α-methylbenzyl)amino]butanoate (946065-13-0) + tert-butyl (3R,αR)-2-(1'-hydroxy)benzyl-3-[N-methyl-N-(α-methylbenzyl)amino]butanoate

Guidance literature:

tert-butyl (3R,αR)-3-[N-methyl-N-(α-methylbenzyl)amino]butanoate; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at 0 ℃; for 2h;

With Trimethyl borate; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

benzaldehyde; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Further stages.;

DOI:10.1016/j.tet.2007.05.015

Reference yield:

tert-butyl (E)-crotonate (79218-15-8) → tert-butyl (2S,3R,1'S,αR)-2-(1'-hydroxy)benzyl-3-[N-methyl-N-(α-methylbenzyl)amino]butanoate (946065-13-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 84 percent / BuLi / hexane; tetrahydrofuran

2.1: BuLi; di-iso-propylamine / hexane; tetrahydrofuran / 2 h / 0 °C

2.2: B(OMe)3 / hexane; tetrahydrofuran / 0.5 h / -78 °C

2.3: 24 percent / tetrahydrofuran; hexane / 2 h / -78 °C

With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane;

DOI:10.1016/j.tet.2007.05.015

Reference yield:

(R)-(+)-N,α-dimethylbenzylamine (5933-40-4) → tert-butyl (2S,3R,1'S,αR)-2-(1'-hydroxy)benzyl-3-[N-methyl-N-(α-methylbenzyl)amino]butanoate (946065-13-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 84 percent / BuLi / hexane; tetrahydrofuran

2.1: BuLi; di-iso-propylamine / hexane; tetrahydrofuran / 2 h / 0 °C

2.2: B(OMe)3 / hexane; tetrahydrofuran / 0.5 h / -78 °C

2.3: 24 percent / tetrahydrofuran; hexane / 2 h / -78 °C

With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane;

DOI:10.1016/j.tet.2007.05.015

upstream raw materials:

tert-butyl (3R,αR)-3-[N-methyl-N-(α-methylbenzyl)amino]butanoate

benzaldehyde

tert-butyl (E)-crotonate

(R)-(+)-N,α-dimethylbenzylamine

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