(R,R,R,R)-N⁽¹⁾-methyl-2-(4-methoxyphenyl)-3-iodo-4-O-methoxymethyl-5-methylpyrrolidine

Base Information

• Chemical Name: (R,R,R,R)-N⁽¹⁾-methyl-2-(4-methoxyphenyl)-3-iodo-4-O-methoxymethyl-5-methylpyrrolidine
• CAS No.: 1346555-96-1
• Molecular Formula: C₁₅H₂₂INO₃
• Molecular Weight: 391.249

Synonyms:(R,R,R,R)-N⁽¹⁾-methyl-2-(4-methoxyphenyl)-3-iodo-4-O-methoxymethyl-5-methylpyrrolidine

Chemical Property of (R,R,R,R)-N⁽¹⁾-methyl-2-(4-methoxyphenyl)-3-iodo-4-O-methoxymethyl-5-methylpyrrolidine

Chemical Property:

Purity/Quality:

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Technology Process of (R,R,R,R)-N⁽¹⁾-methyl-2-(4-methoxyphenyl)-3-iodo-4-O-methoxymethyl-5-methylpyrrolidine

There total 6 articles about (R,R,R,R)-N⁽¹⁾-methyl-2-(4-methoxyphenyl)-3-iodo-4-O-methoxymethyl-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: 54.0%

(3S,4R,αR,E)-1-(4'-methoxyphenyl)-3-O-methoxymethyl-4-[N-methyl-N-(α-methyl-4''-methoxybenzyl)amino]pent-1-ene (1346555-94-9) → (R,R,R,R)-N(1)-methyl-2-(4-methoxyphenyl)-3-iodo-4-O-methoxymethyl-5-methylpyrrolidine (1346555-96-1)

Guidance literature:

With iodine; sodium hydrogencarbonate; In acetonitrile; at 20 ℃; for 20h; optical yield given as %de; diastereoselective reaction;

DOI:10.1016/j.tetlet.2011.09.114

Reference yield:

tert-butyl (R,R,R)-2-O-methoxymethyl-3-[N-methyl-N-(α-methyl-4'-methoxybenzyl)amino]butanoate (1346555-92-7) → (R,R,R,R)-N(1)-methyl-2-(4-methoxyphenyl)-3-iodo-4-O-methoxymethyl-5-methylpyrrolidine (1346555-96-1)

Guidance literature:

Multi-step reaction with 3 steps

1: diisobutylaluminium hydride / dichloromethane / 0.5 h / -78 °C

2: n-butyllithium / tetrahydrofuran / 12.5 h / -78 - 20 °C

3: iodine; sodium hydrogencarbonate / acetonitrile / 20 h / 20 °C

With n-butyllithium; iodine; diisobutylaluminium hydride; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; acetonitrile; 2: Wittig olefination;

DOI:10.1016/j.tetlet.2011.09.114

Reference yield:

C16H25NO4 (1346555-93-8) → (R,R,R,R)-N(1)-methyl-2-(4-methoxyphenyl)-3-iodo-4-O-methoxymethyl-5-methylpyrrolidine (1346555-96-1)

Guidance literature:

Multi-step reaction with 2 steps

1: n-butyllithium / tetrahydrofuran / 12.5 h / -78 - 20 °C

2: iodine; sodium hydrogencarbonate / acetonitrile / 20 h / 20 °C

With n-butyllithium; iodine; sodium hydrogencarbonate; In tetrahydrofuran; acetonitrile; 1: Wittig olefination;

DOI:10.1016/j.tetlet.2011.09.114

upstream raw materials:

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

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

C₁₆H₂₅NO₄

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

Downstream raw materials:

(R,R,R,R)-N⁽¹⁾-methyl-2-(4'-methoxyphenyl)-3-iodo-4-hydroxy-5-methylpyrrolidine hydrochloride

(R,R,R,R)-N(1)-methyl-2-(4'-methoxyphenyl)-3-hydroxy-4-hydroxy-5-methylpyrroli

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

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

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