(2S,3R,4R)-3-Acetoxy-2-(4-methoxy-benzyl)-4-(2,2,2-trichloro-ethoxycarbonyloxy)-pyrrolidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2S,3R,4R)-3-Acetoxy-2-(4-methoxy-benzyl)-4-(2,2,2-trichloro-ethoxycarbonyloxy)-pyrrolidine-1-carboxylic acid benzyl ester
• CAS No.: 111602-18-7
• Molecular Formula: C₂₅H₂₆Cl₃NO₈
• Molecular Weight: 574.842
• Mol file: 111602-18-7.mol

Synonyms:(2S,3R,4R)-3-Acetoxy-2-(4-methoxy-benzyl)-4-(2,2,2-trichloro-ethoxycarbonyloxy)-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property of (2S,3R,4R)-3-Acetoxy-2-(4-methoxy-benzyl)-4-(2,2,2-trichloro-ethoxycarbonyloxy)-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R)-3-Acetoxy-2-(4-methoxy-benzyl)-4-(2,2,2-trichloro-ethoxycarbonyloxy)-pyrrolidine-1-carboxylic acid benzyl ester

There total 7 articles about (2S,3R,4R)-3-Acetoxy-2-(4-methoxy-benzyl)-4-(2,2,2-trichloro-ethoxycarbonyloxy)-pyrrolidine-1-carboxylic acid benzyl ester 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:

2-(p-methoxybenzyl)pyrrole (1963-42-4) → (2S,3R,4R)-3-Acetoxy-2-(4-methoxy-benzyl)-4-(2,2,2-trichloro-ethoxycarbonyloxy)-pyrrolidine-1-carboxylic acid benzyl ester (111602-18-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 67 percent / zinc dust, aq. HCl / ethanol / 1.) 1.5 h, 2.) reflux, 1.5 h

2: 94 percent / aq. NaOH / toluene / 1 h / 3 - 5 °C

3: 82 percent / N-iodosuccinimide, aq. perchloric acid / tetrahydrofuran / 1.) 3-5 deg C, 1 h, 2.) 3-5 deg C -> room temperature, 1 h

4: 92 percent / 5percent KOH, EtOH / 0.5 h

5: 100 percent / hydrogen / 10percent Pd/C / methanol / 2 h

6: trifluoroacetic acid, sodium trifluoroacetate / 16 h / Heating

7: aq. Na₂CO₃ / tetrahydrofuran / 1 h / 3 - 5 °C / pH 9

8: 1.) pyridine, 2.) pyridine / 1.) CH₂Cl₂, 3-5 deg C, 30 min, 2.) 18 h

With pyridine; hydrogenchloride; potassium hydroxide; sodium hydroxide; N-iodo-succinimide; perchloric acid; ethanol; hydrogen; sodium 2,2,2-trifluoroacetate; sodium carbonate; trifluoroacetic acid; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; toluene;

DOI:10.1021/ja00386a039

Reference yield:

benzyl 2-[(4-methoxyphenyl)methyl]-2,5-dihydropyrrole-1-carboxylate (24064-16-2) → (2S,3R,4R)-3-Acetoxy-2-(4-methoxy-benzyl)-4-(2,2,2-trichloro-ethoxycarbonyloxy)-pyrrolidine-1-carboxylic acid benzyl ester (111602-18-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 82 percent / N-iodosuccinimide, aq. perchloric acid / tetrahydrofuran / 1.) 3-5 deg C, 1 h, 2.) 3-5 deg C -> room temperature, 1 h

2: 92 percent / 5percent KOH, EtOH / 0.5 h

3: 100 percent / hydrogen / 10percent Pd/C / methanol / 2 h

4: trifluoroacetic acid, sodium trifluoroacetate / 16 h / Heating

5: aq. Na₂CO₃ / tetrahydrofuran / 1 h / 3 - 5 °C / pH 9

6: 1.) pyridine, 2.) pyridine / 1.) CH₂Cl₂, 3-5 deg C, 30 min, 2.) 18 h

With pyridine; potassium hydroxide; N-iodo-succinimide; perchloric acid; ethanol; hydrogen; sodium 2,2,2-trifluoroacetate; sodium carbonate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1021/ja00386a039

Reference yield:

2-[(4-methoxyphenyl)methyl]-2,5-dihydro-(1H)-pyrrole (22862-67-5) → (2S,3R,4R)-3-Acetoxy-2-(4-methoxy-benzyl)-4-(2,2,2-trichloro-ethoxycarbonyloxy)-pyrrolidine-1-carboxylic acid benzyl ester (111602-18-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 94 percent / aq. NaOH / toluene / 1 h / 3 - 5 °C

2: 82 percent / N-iodosuccinimide, aq. perchloric acid / tetrahydrofuran / 1.) 3-5 deg C, 1 h, 2.) 3-5 deg C -> room temperature, 1 h

3: 92 percent / 5percent KOH, EtOH / 0.5 h

4: 100 percent / hydrogen / 10percent Pd/C / methanol / 2 h

5: trifluoroacetic acid, sodium trifluoroacetate / 16 h / Heating

6: aq. Na₂CO₃ / tetrahydrofuran / 1 h / 3 - 5 °C / pH 9

7: 1.) pyridine, 2.) pyridine / 1.) CH₂Cl₂, 3-5 deg C, 30 min, 2.) 18 h

With pyridine; potassium hydroxide; sodium hydroxide; N-iodo-succinimide; perchloric acid; ethanol; hydrogen; sodium 2,2,2-trifluoroacetate; sodium carbonate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; toluene;

DOI:10.1021/ja00386a039

upstream raw materials:

2-(p-methoxybenzyl)pyrrole

2-[(4-methoxyphenyl)methyl]-2,5-dihydro-(1H)-pyrrole

benzyl 2-[(4-methoxyphenyl)methyl]-2,5-dihydropyrrole-1-carboxylate

rac.-Desacetylanisomycin

Downstream raw materials:

(+/-)-anisomycin