methyl (-)-(1S,3S,3aR,6aS,S_S)-4-oxo-3-phenyl-3a-p-tolylsulfinyloctahydrocyclopenta[c]pyrrole-1-carboxylate

Base Information

• Chemical Name: methyl (-)-(1S,3S,3aR,6aS,S_S)-4-oxo-3-phenyl-3a-p-tolylsulfinyloctahydrocyclopenta[c]pyrrole-1-carboxylate
• CAS No.: 647833-68-9
• Molecular Formula: C₂₂H₂₃NO₄S
• Molecular Weight: 397.495

Synonyms:methyl (-)-(1S,3S,3aR,6aS,S_S)-4-oxo-3-phenyl-3a-p-tolylsulfinyloctahydrocyclopenta[c]pyrrole-1-carboxylate

Chemical Property of methyl (-)-(1S,3S,3aR,6aS,S_S)-4-oxo-3-phenyl-3a-p-tolylsulfinyloctahydrocyclopenta[c]pyrrole-1-carboxylate

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Technology Process of methyl (-)-(1S,3S,3aR,6aS,S_S)-4-oxo-3-phenyl-3a-p-tolylsulfinyloctahydrocyclopenta[c]pyrrole-1-carboxylate

There total 1 articles about methyl (-)-(1S,3S,3aR,6aS,S_S)-4-oxo-3-phenyl-3a-p-tolylsulfinyloctahydrocyclopenta[c]pyrrole-1-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: 38.0%

(E)-N-benzylideneglycine methyl ester (66646-88-6,120238-40-6,138495-05-3) + 2-[(S)-(4-methylphenyl)sulfinyl]cyclopent-2-en-1-one (79681-26-8) → methyl (-)-(1S,3S,3aR,6aS,SS)-4-oxo-3-phenyl-3a-p-tolylsulfinyloctahydrocyclopenta[c]pyrrole-1-carboxylate (647833-68-9) + methyl (-)-(1R,3R,3aS,6aR,SS)-4-oxo-3-phenyl-3a-p-tolylsulfinyloctahydrocyclopenta[c]pyrrole-1-carboxylate (647833-66-7)

Guidance literature:

(E)-N-benzylideneglycine methyl ester; With silver(I) acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; for 0.166667h;

2-[(S)-(4-methylphenyl)sulfinyl]cyclopent-2-en-1-one; In acetonitrile; at 20 ℃; for 0.2h;

DOI:10.1021/jo035369w

Reference yield: 95.0%

methyl (-)-(1S,3S,3aR,6aS,SS)-4-oxo-3-phenyl-3a-p-tolylsulfinyloctahydrocyclopenta[c]pyrrole-1-carboxylate (647833-68-9) → methyl 4-oxo-3-phenyl-2,4,5,6-tetrahydrocyclopenta[c]pyrrole-1-carboxylate

Guidance literature:

In toluene; for 2.5h; Heating;

DOI:10.1021/jo035369w

Reference yield: 84.0%

methyl (-)-(1S,3S,3aR,6aS,SS)-4-oxo-3-phenyl-3a-p-tolylsulfinyloctahydrocyclopenta[c]pyrrole-1-carboxylate (647833-68-9) → methyl (+)-(1S,3R,3aS,6aR)-4-oxo-3-phenyloctahydrocyclopenta[c]pyrrole-1-carboxylate

Guidance literature:

With nickel; In tetrahydrofuran; at -20 ℃; for 0.5h;

DOI:10.1021/jo035369w

upstream raw materials:

(E)-N-benzylideneglycine methyl ester

2-[(S)-(4-methylphenyl)sulfinyl]cyclopent-2-en-1-one

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