1S,2R,5S-menthyl r-2S-methoxycarbonyl-2-methyl-c-5S-(4'-iodo-N-phenylsuphonylindol-3'-yl)pyrrolidine-c-4R-carboxylate

Base Information

• Chemical Name: 1S,2R,5S-menthyl r-2S-methoxycarbonyl-2-methyl-c-5S-(4'-iodo-N-phenylsuphonylindol-3'-yl)pyrrolidine-c-4R-carboxylate
• CAS No.: 161201-95-2
• Molecular Formula: C₃₂H₃₉IN₂O₆S
• Molecular Weight: 706.642

Synonyms:1S,2R,5S-menthyl r-2S-methoxycarbonyl-2-methyl-c-5S-(4'-iodo-N-phenylsuphonylindol-3'-yl)pyrrolidine-c-4R-carboxylate

Chemical Property of 1S,2R,5S-menthyl r-2S-methoxycarbonyl-2-methyl-c-5S-(4'-iodo-N-phenylsuphonylindol-3'-yl)pyrrolidine-c-4R-carboxylate

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Technology Process of 1S,2R,5S-menthyl r-2S-methoxycarbonyl-2-methyl-c-5S-(4'-iodo-N-phenylsuphonylindol-3'-yl)pyrrolidine-c-4R-carboxylate

There total 2 articles about 1S,2R,5S-menthyl r-2S-methoxycarbonyl-2-methyl-c-5S-(4'-iodo-N-phenylsuphonylindol-3'-yl)pyrrolidine-c-4R-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: 52.0%

(1S,2R,5S)‐2‐isopropyl‐5‐methylcyclohexyl acrylate (108945-28-4) + methyl N-(4-iodo-N-phenylsulphonylindolyl-3-methylidene)-alaninate → 1S,2R,5S-menthyl r-2S-methoxycarbonyl-2-methyl-c-5S-(4'-iodo-N-phenylsuphonylindol-3'-yl)pyrrolidine-c-4R-carboxylate (161201-95-2)

Guidance literature:

With silver(I) acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; for 3.5h; Ambient temperature;

DOI:10.1016/0040-4020(94)00956-U

Reference yield:

1-Benzenesulfonyl-4-iodo-1H-indole-3-carbaldehyde → 1S,2R,5S-menthyl r-2S-methoxycarbonyl-2-methyl-c-5S-(4'-iodo-N-phenylsuphonylindol-3'-yl)pyrrolidine-c-4R-carboxylate (161201-95-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / MgSO₄, triethylamine / CH₂Cl₂ / 12 h / Ambient temperature

2: 52 percent / AgOAc, DBU / acetonitrile / 3.5 h / Ambient temperature

With silver(I) acetate; magnesium sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane; acetonitrile;

DOI:10.1016/0040-4020(94)00956-U

Reference yield: 69.0%

carbon monoxide (201230-82-2) + 1S,2R,5S-menthyl r-2S-methoxycarbonyl-2-methyl-c-5S-(4'-iodo-N-phenylsuphonylindol-3'-yl)pyrrolidine-c-4R-carboxylate (161201-95-2) → (7R,9R,9aS)-2-Benzenesulfonyl-7-methyl-6-oxo-2,6,7,8,9,9a-hexahydro-2,6a-diaza-cyclopenta[d]acenaphthylene-7,9-dicarboxylic acid 9-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl) ester 7-methyl ester

Guidance literature:

With palladium diacetate; thallium(I) acetate; triphenylphosphine; In acetonitrile; for 60h; Heating;

DOI:10.1016/0040-4020(94)00956-U

upstream raw materials:

(1S,2R,5S)‐2‐isopropyl‐5‐methylcyclohexyl acrylate

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