(2R,3aR,8aS)-2-phenylselanyl-8-(toluene-4-sulfonyl)-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid methyl ester

Base Information

• Chemical Name: (2R,3aR,8aS)-2-phenylselanyl-8-(toluene-4-sulfonyl)-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid methyl ester
• CAS No.: 709030-60-4
• Molecular Formula: C₂₅H₂₄N₂O₄SSe
• Molecular Weight: 527.503

Synonyms:(2R,3aR,8aS)-2-phenylselanyl-8-(toluene-4-sulfonyl)-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid methyl ester

Chemical Property of (2R,3aR,8aS)-2-phenylselanyl-8-(toluene-4-sulfonyl)-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (2R,3aR,8aS)-2-phenylselanyl-8-(toluene-4-sulfonyl)-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid methyl ester

There total 2 articles about (2R,3aR,8aS)-2-phenylselanyl-8-(toluene-4-sulfonyl)-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid methyl ester 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:

diphenyl diselenide (1666-13-3) + 8-(toluene-4-sulfonyl)-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 1-methyl ester → (2R,3aR,8aS)-2-phenylselanyl-8-(toluene-4-sulfonyl)-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid methyl ester (709030-60-4) + (2S,3aR,8aS)-2-phenylselenyl-8-(toluene-4-sulfonyl)-3,3a,8,8a-hexahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid methyl ester

Guidance literature:

8-(toluene-4-sulfonyl)-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 1-methyl ester; With 1-oxa-2-oxo-3-thiaindolizinium chloride; triethylamine; In dichloromethane; at 20 ℃; for 2h;

diphenyl diselenide; In dichloromethane; for 3h; Photolysis;

DOI:10.1021/jo049757p

Reference yield:

C20H20N2O6S + diphenyl diselenide (1666-13-3) → (2R,3aR,8aS)-2-phenylselanyl-8-(toluene-4-sulfonyl)-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid methyl ester (709030-60-4)

Guidance literature:

With 2-oxo-[1,4,2]oxathiazolo[2,3-a]pyridin-4-ium chloride; triethylamine;

DOI:10.1016/j.tetlet.2009.01.034

Reference yield: 94.4%

trimethylsilyl cyanide (7677-24-9) + (2R,3aR,8aS)-2-phenylselanyl-8-(toluene-4-sulfonyl)-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid methyl ester (709030-60-4) → (2S,3aR,8aS)-2-cyano-8-(toluene-4-sulfonyl)-3,3a,8,8a-hexahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid methyl ester (709030-64-8)

Guidance literature:

With tin(IV) chloride; In dichloromethane; at -30 ℃; for 1.5h;

DOI:10.1021/jo049757p

upstream raw materials:

diphenyl diselenide

Downstream raw materials:

(2S,3aR,8aS)-2-cyano-8-(toluene-4-sulfonyl)-3,3a,8,8a-hexahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid methyl ester

C₁₇H₁₆N₂O₂S

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