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

Base Information

• Chemical Name: (2R,3S,4S,5R)-N⁽¹⁾-methyl-2-acetoxy-3-(4'-methoxyphenyl)-4-O-methoxymethyl-5-methylpyrrolidine
• CAS No.: 1346555-99-4
• Molecular Formula: C₁₇H₂₅NO₅
• Molecular Weight: 323.389

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

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

Chemical Property:

Purity/Quality:

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

There total 10 articles about (2R,3S,4S,5R)-N⁽¹⁾-methyl-2-acetoxy-3-(4'-methoxyphenyl)-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:

(R,R,R,R)-N(1)-methyl-2-(4-methoxyphenyl)-3-iodo-4-O-methoxymethyl-5-methylpyrrolidine (1346555-96-1) + silver(I) acetate (563-63-3) → (R,R,R,R)-N(1)-methyl-2-(4'-methoxyphenyl)-3-acetoxy-4-O-methoxymethyl-5-methylpyrrolidine (1346555-98-3) + (2R,3S,4S,5R)-N(1)-methyl-2-acetoxy-3-(4'-methoxyphenyl)-4-O-methoxymethyl-5-methylpyrrolidine (1346555-99-4)

Guidance literature:

With acetic acid; at 40 ℃; for 24h; 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-methyl-N-(α-methyl-4'-methoxybenzyl)amino]butanoate (1346555-91-6) → (2R,3S,4S,5R)-N(1)-methyl-2-acetoxy-3-(4'-methoxyphenyl)-4-O-methoxymethyl-5-methylpyrrolidine (1346555-99-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C

1.2: 12 h / 20 °C

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

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

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

5.1: 24 h / 40 °C

With n-butyllithium; iodine; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 3.1: Wittig olefination;

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) → (2R,3S,4S,5R)-N(1)-methyl-2-acetoxy-3-(4'-methoxyphenyl)-4-O-methoxymethyl-5-methylpyrrolidine (1346555-99-4)

Guidance literature:

Multi-step reaction with 4 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

4: 24 h / 40 °C

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

DOI:10.1016/j.tetlet.2011.09.114

upstream raw materials:

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

silver(I) acetate

acetic acid

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

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