ethyl 2-((3S,4R,5S)-4-methyl-4-nitro-5-phenyl-1-tosylpyrrolidin-3-yl)acetate

Base Information

• Chemical Name: ethyl 2-((3S,4R,5S)-4-methyl-4-nitro-5-phenyl-1-tosylpyrrolidin-3-yl)acetate
• CAS No.: 1369894-15-4
• Molecular Formula: C₂₂H₂₆N₂O₆S
• Molecular Weight: 446.524

Synonyms:ethyl 2-((3S,4R,5S)-4-methyl-4-nitro-5-phenyl-1-tosylpyrrolidin-3-yl)acetate

Chemical Property of ethyl 2-((3S,4R,5S)-4-methyl-4-nitro-5-phenyl-1-tosylpyrrolidin-3-yl)acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of ethyl 2-((3S,4R,5S)-4-methyl-4-nitro-5-phenyl-1-tosylpyrrolidin-3-yl)acetate

There total 4 articles about ethyl 2-((3S,4R,5S)-4-methyl-4-nitro-5-phenyl-1-tosylpyrrolidin-3-yl)acetate 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:

1-phenyl-2-nitroprop-1-ene (705-60-2,18315-84-9,58321-79-2) + (E)-ethyl 4-(4-methylphenylsulfonamido)but-2-enoate → ethyl 2-((3R,4R,5S)-4-methyl-4-nitro-5-phenyl-1-tosylpyrrolidin-3-yl)acetate (1369894-16-5) + ethyl 2-((3S,4R,5S)-4-methyl-4-nitro-5-phenyl-1-tosylpyrrolidin-3-yl)acetate (1369894-15-4) + ethyl 2-((3R,4S,5R)-4-methyl-4-nitro-5-phenyl-1-tosylpyrrolidin-3-yl)acetate + ethyl 2-((3S,4S,5R)-4-methyl-4-nitro-5-phenyl-1-tosylpyrrolidin-3-yl)acetate

Guidance literature:

With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-((2S,4S,8R)-8-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methyl)thiourea; In toluene; at 60 ℃; for 72h; optical yield given as %ee; enantioselective reaction;

DOI:10.1016/j.tetasy.2012.01.021

Reference yield:

4-bromo-trans-crotonic acid ethyl ester (37746-78-4) → ethyl 2-((3R,4R,5S)-4-methyl-4-nitro-5-phenyl-1-tosylpyrrolidin-3-yl)acetate (1369894-16-5) + ethyl 2-((3S,4R,5S)-4-methyl-4-nitro-5-phenyl-1-tosylpyrrolidin-3-yl)acetate (1369894-15-4) + ethyl 2-((3R,4S,5R)-4-methyl-4-nitro-5-phenyl-1-tosylpyrrolidin-3-yl)acetate + ethyl 2-((3S,4S,5R)-4-methyl-4-nitro-5-phenyl-1-tosylpyrrolidin-3-yl)acetate

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 60 °C / Inert atmosphere

2: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere; Cooling with ice

3: 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-((2S,4S,8R)-8-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methyl)thiourea / toluene / 72 h / 60 °C

With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-((2S,4S,8R)-8-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methyl)thiourea; potassium carbonate; trifluoroacetic acid; sodium iodide; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tetasy.2012.01.021

Reference yield:

N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide (18303-04-3) → ethyl 2-((3R,4R,5S)-4-methyl-4-nitro-5-phenyl-1-tosylpyrrolidin-3-yl)acetate (1369894-16-5) + ethyl 2-((3S,4R,5S)-4-methyl-4-nitro-5-phenyl-1-tosylpyrrolidin-3-yl)acetate (1369894-15-4) + ethyl 2-((3R,4S,5R)-4-methyl-4-nitro-5-phenyl-1-tosylpyrrolidin-3-yl)acetate + ethyl 2-((3S,4S,5R)-4-methyl-4-nitro-5-phenyl-1-tosylpyrrolidin-3-yl)acetate

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 60 °C / Inert atmosphere

2: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere; Cooling with ice

3: 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-((2S,4S,8R)-8-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methyl)thiourea / toluene / 72 h / 60 °C

With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-((2S,4S,8R)-8-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methyl)thiourea; potassium carbonate; trifluoroacetic acid; sodium iodide; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tetasy.2012.01.021

upstream raw materials:

1-phenyl-2-nitroprop-1-ene

(E)-ethyl 4-(N-(tert-butoxycarbonyl)-4-methylphenylsulfonamido)but-2-enoate

4-bromo-trans-crotonic acid ethyl ester

N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide

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