(2S,3R)-2-methyl-4-methylene-2-phenyl-1-tosylpyrrolidine-3-carbonitrile

Base Information

• Chemical Name: (2S,3R)-2-methyl-4-methylene-2-phenyl-1-tosylpyrrolidine-3-carbonitrile
• CAS No.: 1231765-26-6
• Molecular Formula: C₂₀H₂₀N₂O₂S
• Molecular Weight: 352.457

Synonyms:(2S,3R)-2-methyl-4-methylene-2-phenyl-1-tosylpyrrolidine-3-carbonitrile

Chemical Property of (2S,3R)-2-methyl-4-methylene-2-phenyl-1-tosylpyrrolidine-3-carbonitrile

Chemical Property:

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Technology Process of (2S,3R)-2-methyl-4-methylene-2-phenyl-1-tosylpyrrolidine-3-carbonitrile

There total 3 articles about (2S,3R)-2-methyl-4-methylene-2-phenyl-1-tosylpyrrolidine-3-carbonitrile 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: 91.0%

4-methyl-N-(1-phenylethylidene)benzenesulfonamide (24865-83-6) + 3-acetoxy-3-cyano-2-trimethylsilylmethylpropene (94111-03-2) → (2S,3R)-2-methyl-4-methylene-2-phenyl-1-tosylpyrrolidine-3-carbonitrile (1231765-26-6)

Guidance literature:

With O,O'-(R)-(1,1'-dinaphthyl-2,2'-diyl)-N-((R,R)-2,5-di(naphthyl)pyrrolidine); allyl(cyclopentadiene)palladium(II); In toluene; at 4 ℃; optical yield given as %ee; enantioselective reaction;

DOI:10.1021/ja102102d

Reference yield:

4-methyl-N-(1-phenylethylidene)benzenesulfonamide (24865-83-6) + 3-acetoxy-3-cyano-2-trimethylsilylmethylpropene (94111-03-2) → (2S,3R)-2-methyl-4-methylene-2-phenyl-1-tosylpyrrolidine-3-carbonitrile (1231765-26-6) + (2S,3S)-2-methyl-4-methylene-2-phenyl-1-tosylpyrrolidine-3-carbonitrile + (2R,3R)-2-methyl-4-methylene-2-phenyl-1-tosylpyrrolidine-3-carbonitrile (1231765-39-1)

Guidance literature:

With allyl(cyclopentadiene)palladium(II); C₃₅H₂₆NO₂P; In toluene; at 4 ℃; optical yield given as %ee; enantioselective reaction;

DOI:10.1021/ja102102d

Reference yield:

4-methyl-N-(1-phenylethylidene)benzenesulfonamide (24865-83-6) + 3-acetoxy-3-cyano-2-trimethylsilylmethylpropene (94111-03-2) → (2S,3R)-2-methyl-4-methylene-2-phenyl-1-tosylpyrrolidine-3-carbonitrile (1231765-26-6) + (2S,3S)-2-methyl-4-methylene-2-phenyl-1-tosylpyrrolidine-3-carbonitrile + (2R,3R)-2-methyl-4-methylene-2-phenyl-1-tosylpyrrolidine-3-carbonitrile (1231765-39-1) + (2R,3S)-2-methyl-4-methylene-2-phenyl-1-tosylpyrrolidine-3-carbonitrile

Guidance literature:

With O,O'-(R)-(1,1'-dinaphthyl-2,2'-diyl)-N,N'-di-(R,R)-1-phenylethylphosphoramidite; allyl(cyclopentadiene)palladium(II); In toluene; at 4 ℃; optical yield given as %ee; enantioselective reaction;

DOI:10.1021/ja102102d

upstream raw materials:

4-methyl-N-(1-phenylethylidene)benzenesulfonamide

3-acetoxy-3-cyano-2-trimethylsilylmethylpropene

Downstream raw materials:

C₃₆H₄₀N₂O₃SSi

(2S,3R,4S)-4-((tert-butyldiphenylsilyloxy)methyl)-2-methyl-2-phenylpyrrolidine-3-carbonitrile

C₂₀H₂₂N₂O₃S

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