(R,R,R)-2-O-methoxymethyl-3-[N-benzyl-N-(α-methyl-4'-methoxybenzyl)amino]butanal

Base Information

• Chemical Name: (R,R,R)-2-O-methoxymethyl-3-[N-benzyl-N-(α-methyl-4'-methoxybenzyl)amino]butanal
• CAS No.: 1376623-13-0
• Molecular Formula: C₂₂H₂₉NO₄
• Molecular Weight: 371.477

Synonyms:(R,R,R)-2-O-methoxymethyl-3-[N-benzyl-N-(α-methyl-4'-methoxybenzyl)amino]butanal

Chemical Property of (R,R,R)-2-O-methoxymethyl-3-[N-benzyl-N-(α-methyl-4'-methoxybenzyl)amino]butanal

Chemical Property:

Purity/Quality:

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Technology Process of (R,R,R)-2-O-methoxymethyl-3-[N-benzyl-N-(α-methyl-4'-methoxybenzyl)amino]butanal

There total 3 articles about (R,R,R)-2-O-methoxymethyl-3-[N-benzyl-N-(α-methyl-4'-methoxybenzyl)amino]butanal 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:

tert-butyl (R,R,R)-2-O-methoxymethyl-3-[N-benzyl-N-(α-methyl-4'-methoxybenzyl)amino]butanoate (1376622-90-0) → (R,R,R)-2-O-methoxymethyl-3-[N-benzyl-N-(α-methyl-4'-methoxybenzyl)amino]butanal (1376623-13-0)

Guidance literature:

tert-butyl (R,R,R)-2-O-methoxymethyl-3-[N-benzyl-N-(α-methyl-4'-methoxybenzyl)amino]butanoate; With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 0.5h; Inert atmosphere;

With methanol; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2012.03.045

Reference yield:

tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methyl-4'-methoxybenzyl)amino]butanoate (1376622-69-3) → (R,R,R)-2-O-methoxymethyl-3-[N-benzyl-N-(α-methyl-4'-methoxybenzyl)amino]butanal (1376623-13-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

1.2: 12 h / 0 - 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

With sodium hydride; diisobutylaluminium hydride; In dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1016/j.tet.2012.03.045

Reference yield:

(R)-N-benzyl-N-(α-methyl-p-methoxybenzyl)amine (14429-03-9,120343-46-6,140408-66-8) → (R,R,R)-2-O-methoxymethyl-3-[N-benzyl-N-(α-methyl-4'-methoxybenzyl)amino]butanal (1376623-13-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

1.2: 2 h / -78 °C / Inert atmosphere

1.3: 12 h / -78 - 20 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

2.2: 12 h / 0 - 20 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

With n-butyllithium; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1016/j.tet.2012.03.045

upstream raw materials:

tert-butyl (R,R,R)-2-O-methoxymethyl-3-[N-benzyl-N-(α-methyl-4'-methoxybenzyl)amino]butanoate

tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methyl-4'-methoxybenzyl)amino]butanoate

(R)-N-benzyl-N-(α-methyl-p-methoxybenzyl)amine

Downstream raw materials:

(R,R,R,R)-N⁽¹⁾-benzyl-2-(4'-methoxyphenyl)-3-acetoxy-4-O-methoxymethyl-5-methylpyrrolidine

(R,R,R,R)-N⁽¹⁾-benzyl-2-(4'-methoxyphenyl)-3-acetoxy-4-hydroxy-5-methylpyrrolidine

(R,R,R,R)-N⁽¹⁾-benzyl-2-(4'-methoxyphenyl)-3,4-diacetoxy-5-methylpyrrolidine

(R,R,R,R)-N⁽¹⁾-2-(4'-methoxyphenyl)-3,4-dihydroxy-5-methylpyrrolidine

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