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

Base Information

• Chemical Name: (2S,3R,4S,5S)-methyl 3-(4-chlorophenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate
• CAS No.: 1223020-41-4
• Molecular Formula: C₁₈H₁₇ClN₂O₄
• Molecular Weight: 360.797
• Mol file: 1223020-41-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

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

There total 3 articles about (2S,3R,4S,5S)-methyl 3-(4-chlorophenyl)-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: 40.0%

1-chloro-4-(2-nitrovinyl)benzene (706-07-0,5153-70-8) + methyl 2-(benzylideneamino)acetate (66646-88-6) → 3-(4-chlorophenyl)-2-(methoxycarbonyl)-4-nitro-5-phenylpyrrolidine + (2S,3R,4S,5S)-methyl 3-(4-chlorophenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate (1223020-41-4)

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:

1-chloro-4-(2-nitrovinyl)benzene (706-07-0,5153-70-8) + methyl 2-(benzylideneamino)acetate (66646-88-6) → (2S,3R,4S,5S)-methyl 3-(4-chlorophenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate (1223020-41-4) + (2R,3S,4R,5R)-methyl 3-(4-chlorophenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate

Guidance literature:

With copper(I) triflate benzene complex; DBN; brucine diol; In tetrahydrofuran; at -15 ℃; Overall yield = 95 %; Overall yield = 171 mg; enantioselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.5b00277

Reference yield:

1-nitro-2-(4-chlorophenyl)ethylene (101671-01-6,5153-70-8) + methyl 2-(benzylideneamino)acetate (66646-88-6) → (2S,3R,4S,5S)-methyl 3-(4-chlorophenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate (1223020-41-4) + (2R,3S,4R,5R)-methyl 3-(4-chlorophenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate

Guidance literature:

With 2,6-bis((2R,4S,5S)-1-benzyl-4,5-diphenylimidazolidin-2-yl)pyridine; copper(II) bis(trifluoromethanesulfonate); caesium carbonate; triethylamine; In 1,4-dioxane; at 20 ℃; for 22h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ja100265j

upstream raw materials:

1-nitro-2-(4-chlorophenyl)ethylene

methyl 2-(benzylideneamino)acetate

1-chloro-4-(2-nitrovinyl)benzene