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

Base Information

• Chemical Name: (R,R,R,R)-N⁽¹⁾-benzyl-2-(4'-methoxyphenyl)-3-iodo-4-benzyloxy-5-methylpyrrolidine
• CAS No.: 1376622-85-3
• Molecular Formula: C₂₆H₂₈INO₂
• Molecular Weight: 513.418

Synonyms:(R,R,R,R)-N⁽¹⁾-benzyl-2-(4'-methoxyphenyl)-3-iodo-4-benzyloxy-5-methylpyrrolidine

Chemical Property of (R,R,R,R)-N⁽¹⁾-benzyl-2-(4'-methoxyphenyl)-3-iodo-4-benzyloxy-5-methylpyrrolidine

Chemical Property:

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Technology Process of (R,R,R,R)-N⁽¹⁾-benzyl-2-(4'-methoxyphenyl)-3-iodo-4-benzyloxy-5-methylpyrrolidine

There total 6 articles about (R,R,R,R)-N⁽¹⁾-benzyl-2-(4'-methoxyphenyl)-3-iodo-4-benzyloxy-5-methylpyrrolidine 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: 41.0%

(3S,4R,αR,E)-1-(4'-methoxyphenyl)-3-benzyloxy-4-[N-benzyl-N-(α-methyl-4''-methoxybenzyl)-amino]pent-1-ene (1376622-81-9) → (R,R,R,R)-N(1)-benzyl-2-(4'-methoxyphenyl)-3-iodo-4-benzyloxy-5-methylpyrrolidine (1376622-85-3)

Guidance literature:

With iodine; sodium hydrogencarbonate; In acetonitrile; at -20 - 20 ℃; for 22h; optical yield given as %de; 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,R)-N(1)-benzyl-2-(4'-methoxyphenyl)-3-iodo-4-benzyloxy-5-methylpyrrolidine (1376622-85-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere

1.2: 12 h / 20 °C / Inert atmosphere

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2.2: 0 °C / Inert atmosphere

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.33 h / -78 °C / Inert atmosphere

3.2: 1 h / -78 - 20 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran / 0.5 h / 78 °C / Inert atmosphere

4.2: -78 - 20 °C / Inert atmosphere

5.1: iodine; sodium hydrogencarbonate / acetonitrile / 22 h / -20 - 20 °C / Inert atmosphere

With lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; iodine; sodium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; acetonitrile; mineral oil; 3.1: Swern oxidation / 3.2: Swern oxidation / 4.2: Wittig reaction;

DOI:10.1016/j.tet.2012.03.045

Reference yield:

C27H31NO3 (1376622-78-4) → (R,R,R,R)-N(1)-benzyl-2-(4'-methoxyphenyl)-3-iodo-4-benzyloxy-5-methylpyrrolidine (1376622-85-3)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: -78 - 20 °C / Inert atmosphere

2.1: iodine; sodium hydrogencarbonate / acetonitrile / 22 h / -20 - 20 °C / Inert atmosphere

With n-butyllithium; iodine; sodium hydrogencarbonate; In tetrahydrofuran; acetonitrile; 1.2: Wittig reaction;

DOI:10.1016/j.tet.2012.03.045

upstream raw materials:

(3S,4R,αR,E)-1-(4'-methoxyphenyl)-3-benzyloxy-4-[N-benzyl-N-(α-methyl-4''-methoxybenzyl)-amino]pent-1-ene

C₂₇H₃₁NO₃

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

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

Downstream raw materials:

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

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