(2S,3R,4S,5S)-methyl 3-(4-methoxyphenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate

Base Information

• Chemical Name: (2S,3R,4S,5S)-methyl 3-(4-methoxyphenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate
• CAS No.: 888330-67-4
• Molecular Formula: C₁₉H₂₀N₂O₅
• Molecular Weight: 356.378
• Mol file: 888330-67-4.mol

Synonyms:(2S,3R,4S,5S)-methyl 3-(4-methoxyphenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate

Chemical Property of (2S,3R,4S,5S)-methyl 3-(4-methoxyphenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,5S)-methyl 3-(4-methoxyphenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate

There total 5 articles about (2S,3R,4S,5S)-methyl 3-(4-methoxyphenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate 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: 64.0%

1-methoxy-4-(2-nitro-vinyl)-benzene (3179-10-0) + methyl 2-(benzylideneamino)acetate (66646-88-6) → (2S,3R,4S,5S)-methyl 3-(4-methoxyphenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate (888330-67-4) + (2S,3S,4R,5S)-methyl 3-(4-methoxyphenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate (888330-57-2)

Guidance literature:

With (R,Sp)-ThioClickFerrophos; silver(I) acetate; In 1,4-dioxane; at 20 ℃; for 10h; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2015.08.002

Reference yield:

(E)-1-methoxy-4-(2-nitrovinyl)benzene (3179-10-0,5576-97-6) + (E)-N-benzylideneglycine methyl ester (66646-88-6,120238-40-6,138495-05-3) → (2S,3R,4S,5S)-methyl 3-(4-methoxyphenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate (888330-67-4) + (2S,3S,4R,5S)-methyl 3-(4-methoxyphenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate (888330-57-2)

Guidance literature:

With silver(I) acetate; triethylamine; In acetonitrile; at 20 ℃;

Reference yield:

(E)-1-methoxy-4-(2-nitrovinyl)benzene (3179-10-0,5576-97-6) + (E)-N-benzylideneglycine methyl ester (66646-88-6,120238-40-6,138495-05-3) → 2-(methoxycarbonyl)-3-(4-methoxyphenyl)-4-nitro-5-phenylpyrrolidine + (2S,3R,4S,5S)-methyl 3-(4-methoxyphenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate (888330-67-4) + (2R,3S,4R,5R)-methyl 3-(4-methoxyphenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate + (2S,3S,4R,5S)-methyl 3-(4-methoxyphenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate (888330-57-2)

Guidance literature:

With tetrakis(acetonitrile)copper(I) perchlorate; 4 A molecular sieve; potassium tert-butylate; (2-(bis(3,5-bis(trifluoromethyl)phenyl)phosphino)-3-((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)cyclopenta-2,4-dien-1-yl)(cyclopenta-2,4-dien-1-yl)iron; In tetrahydrofuran; at 0 ℃; Title compound not separated from byproducts;

DOI:10.1002/anie.200503672

upstream raw materials:

(E)-1-methoxy-4-(2-nitrovinyl)benzene

(E)-N-benzylideneglycine methyl ester

methyl 2-(benzylideneamino)acetate

1-methoxy-4-(2-nitro-vinyl)-benzene

Downstream raw materials:

methyl 3-(4-methoxyphenyl)-5-phenyl-1H-pyrrole-2-carboxylate

5-phenyl-3-(4-methoxyphenyl)-2-methoxycarbonyl-4-nitro-1H-pyrrole