(2S,3R,4S,5S)-methyl 5-(naphthalen-1-yl)-4-nitro-3-phenylpyrrolidine-2-carboxylate

Base Information

• Chemical Name: (2S,3R,4S,5S)-methyl 5-(naphthalen-1-yl)-4-nitro-3-phenylpyrrolidine-2-carboxylate
• CAS No.: 1223020-38-9
• Molecular Formula: C₂₂H₂₀N₂O₄
• Molecular Weight: 376.412
• Mol file: 1223020-38-9.mol

Synonyms:(2S,3R,4S,5S)-methyl 5-(naphthalen-1-yl)-4-nitro-3-phenylpyrrolidine-2-carboxylate

Chemical Property of (2S,3R,4S,5S)-methyl 5-(naphthalen-1-yl)-4-nitro-3-phenylpyrrolidine-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of (2S,3R,4S,5S)-methyl 5-(naphthalen-1-yl)-4-nitro-3-phenylpyrrolidine-2-carboxylate

There total 3 articles about (2S,3R,4S,5S)-methyl 5-(naphthalen-1-yl)-4-nitro-3-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:

(2-nitroethenyl)benzene (102-96-5) + methyl 2-(1-naphthalenemethyleneamino)acetate → (2S,3R,4S,5S)-methyl 5-(naphthalen-1-yl)-4-nitro-3-phenylpyrrolidine-2-carboxylate (1223020-38-9) + (2R,3S,4R,5R)-methyl 5-(naphthalen-1-yl)-4-nitro-3-phenylpyrrolidine-2-carboxylate

Guidance literature:

With (R,Sp)-ThioClickFerrophos; silver(I) acetate; In 1,4-dioxane; at 20 ℃; for 10h; Overall yield = 80 %; Overall yield = 60.2 mg; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2015.08.002

Reference yield:

nitrostyrene (5153-67-3) + methyl 2-(1-naphthalenemethyleneamino)acetate → (2S,3R,4S,5S)-methyl 5-(naphthalen-1-yl)-4-nitro-3-phenylpyrrolidine-2-carboxylate (1223020-38-9) + (2R,3S,4R,5R)-methyl 5-(naphthalen-1-yl)-4-nitro-3-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; In 1,4-dioxane; at 20 ℃; for 22h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ja100265j

Reference yield:

(2-nitroethenyl)benzene (102-96-5) + methyl 2-(1-naphthalenemethyleneamino)acetate → (2S,3R,4S,5S)-methyl 5-(naphthalen-1-yl)-4-nitro-3-phenylpyrrolidine-2-carboxylate (1223020-38-9) + (2S,3R,4S,5R)-methyl 5-(naphthalen-1-yl)-4-nitro-3-phenylpyrrolidine-2-carboxylate (1257558-73-8)

Guidance literature:

With 2-{[(1S)-N-{[(4S,5S)-4,5-dihydro-4,5-diphenyl-1-tosyl-1H-imidazol-2-yl]methyl}-1-phenylethanamino]methyl}-4,6-dibromophenol; nickel(II) acetate tetrahydrate; potassium carbonate; In acetonitrile; at -10 ℃; for 42h; optical yield given as %ee; stereoselective reaction;

DOI:10.1002/anie.201004098

upstream raw materials:

nitrostyrene

(2-nitroethenyl)benzene