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

Base Information

• Chemical Name: 1S,2R,5S-menthyl 2S-benzyl-r-2-methoxycarbonyl-c-5S-(4'-iodo-N-phenylsuphonylindol-3'-yl)pyrrolidine-c-4R-carboxylate
• CAS No.: 161201-96-3
• Molecular Formula: C₃₈H₄₃IN₂O₆S
• Molecular Weight: 782.74

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

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

Chemical Property:

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

There total 3 articles about 1S,2R,5S-menthyl 2S-benzyl-r-2-methoxycarbonyl-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: 51.0%

(1S,2R,5S)‐2‐isopropyl‐5‐methylcyclohexyl acrylate (108945-28-4) + methyl N-(4-iodo-N-phenylsulphonylindolyl-3-methylidene)-phenylalaninate → 1S,2R,5S-menthyl 2S-benzyl-r-2-methoxycarbonyl-c-5S-(4'-iodo-N-phenylsuphonylindol-3'-yl)pyrrolidine-c-4R-carboxylate (161201-96-3)

Guidance literature:

With silver(I) acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; for 2.5h; Ambient temperature;

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

Reference yield:

methyl 2-amino-3-phenylpropanoate hydrochloride (5619-07-8) → 1S,2R,5S-menthyl 2S-benzyl-r-2-methoxycarbonyl-c-5S-(4'-iodo-N-phenylsuphonylindol-3'-yl)pyrrolidine-c-4R-carboxylate (161201-96-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / MgSO₄, triethylamine / CH₂Cl₂ / 12 h / Ambient temperature

2: 51 percent / AgOAc, DBU / acetonitrile / 2.5 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:

1-Benzenesulfonyl-4-iodo-1H-indole-3-carbaldehyde → 1S,2R,5S-menthyl 2S-benzyl-r-2-methoxycarbonyl-c-5S-(4'-iodo-N-phenylsuphonylindol-3'-yl)pyrrolidine-c-4R-carboxylate (161201-96-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / MgSO₄, triethylamine / CH₂Cl₂ / 12 h / Ambient temperature

2: 51 percent / AgOAc, DBU / acetonitrile / 2.5 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

upstream raw materials:

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

methyl 2-amino-3-phenylpropanoate hydrochloride

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