diethyl (3S,4R,5R,1'E)-4-formyl-3-phenyl-5-styrylpyrrolidine-2,2-dicarboxylate

Base Information

• Chemical Name: diethyl (3S,4R,5R,1'E)-4-formyl-3-phenyl-5-styrylpyrrolidine-2,2-dicarboxylate
• CAS No.: 1391849-75-4
• Molecular Formula: C₂₅H₂₇NO₅
• Molecular Weight: 421.493
• Mol file: 1391849-75-4.mol

Synonyms:diethyl (3S,4R,5R,1'E)-4-formyl-3-phenyl-5-styrylpyrrolidine-2,2-dicarboxylate

Chemical Property of diethyl (3S,4R,5R,1'E)-4-formyl-3-phenyl-5-styrylpyrrolidine-2,2-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diethyl (3S,4R,5R,1'E)-4-formyl-3-phenyl-5-styrylpyrrolidine-2,2-dicarboxylate

There total 1 articles about diethyl (3S,4R,5R,1'E)-4-formyl-3-phenyl-5-styrylpyrrolidine-2,2-dicarboxylate 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:

(E)-3-phenylpropenal (14371-10-9) + dimethyl 2-aminomalonate (53704-09-9) → diethyl (3S,4R,5R,1'E)-4-formyl-3-phenyl-5-styrylpyrrolidine-2,2-dicarboxylate (1391849-75-4) + diethyl (3S,4R,5S,1'E)-4-formyl-3-phenyl-5-styrylpyrrolidine-2,2-dicarboxylate

Guidance literature:

With (S)-diphenylprolinol; water; In tetrahydrofuran; at 0 - 4 ℃; optical yield given as %de; enantioselective reaction;

DOI:10.1002/chem.201103015

Reference yield: 85.0%

diethyl (3S,4R,5R,1'E)-4-formyl-3-phenyl-5-styrylpyrrolidine-2,2-dicarboxylate (1391849-75-4) → diethyl (3S,4R,5R,1'E)-4-hydroxymethyl-3-phenyl-5-styrylpyrrolidine-2,2-dicarboxylate (1391849-82-3)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.5h;

DOI:10.1002/chem.201103015

Reference yield:

diethyl (3S,4R,5R,1'E)-4-formyl-3-phenyl-5-styrylpyrrolidine-2,2-dicarboxylate (1391849-75-4) → C25H27NO7 (1391850-04-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium tetrahydroborate / methanol / 0.5 h / 0 °C

2.1: 1H-imidazole; dmap / tetrahydrofuran / 20 °C

3.1: potassium carbonate / acetonitrile / 2 h / Reflux

3.2: 2 h / Reflux

4.1: ozone / dichloromethane / -78 °C

4.2: 1 h / -78 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; tetrabutyl ammonium fluoride; potassium carbonate; ozone; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1002/chem.201103015

upstream raw materials:

(E)-3-phenylpropenal

dimethyl 2-aminomalonate

Downstream raw materials:

diethyl (3S,4R,5R,1'E)-4-hydroxymethyl-3-phenyl-5-styrylpyrrolidine-2,2-dicarboxylate

C₂₅H₂₇NO₇

diethyl (3S,3aR,6aS)-1-benzoyl-6-oxo-3-phenyltetrahydro-1H-furo[3,4-b]pyrrole-2,2(3H)-dicarboxylate

diethyl (3S,3aR,6aS)-1-benzoyl-3-phenyltetrahydro-1H-furo[3,4-b]pyrrole-2,2(3H)-dicarboxylate