dimethyl (2S,3aR,8aS)-2-ethyl-8-phenylsulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

Base Information

• Chemical Name: dimethyl (2S,3aR,8aS)-2-ethyl-8-phenylsulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate
• CAS No.: 146138-83-2
• Molecular Formula: C₂₂H₂₄N₂O₆S
• Molecular Weight: 444.508

Synonyms:dimethyl (2S,3aR,8aS)-2-ethyl-8-phenylsulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

Chemical Property of dimethyl (2S,3aR,8aS)-2-ethyl-8-phenylsulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

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Technology Process of dimethyl (2S,3aR,8aS)-2-ethyl-8-phenylsulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

There total 1 articles about dimethyl (2S,3aR,8aS)-2-ethyl-8-phenylsulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate 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:

dimethyl (2S,3aR,8aS)-8-benzenesulphonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-1,2-dicarboxylate (136057-11-9) + ethyl iodide (75-03-6) → dimethyl (2S,3aR,8aS)-2-ethyl-8-phenylsulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (146138-83-2)

Guidance literature:

With lithium diisopropyl amide; Yield given. Multistep reaction; 1.) THF, -78 deg C, 10 min, 2.) THF, from -78 deg C to RT;

Reference yield: 100.0%

dimethyl (2S,3aR,8aS)-2-ethyl-8-phenylsulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (146138-83-2) → (αS)-1-benzenesulfonyl-α-ethyl-Nb-methoxycarbonyltryptophan methyl ester (146138-85-4)

Guidance literature:

With trifluoroacetic acid; for 1h; Ambient temperature;

Reference yield: 72.0%

dimethyl (2S,3aR,8aS)-2-ethyl-8-phenylsulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (146138-83-2) → (+)-(2S,3aR,8aS)-2-Ethyl-1-(methoxycarbonyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-2-carboxylic acid

Guidance literature:

With potassium hydroxide; In methanol; for 12h;

DOI:10.1021/jo00124a055

upstream raw materials:

dimethyl (2S,3aR,8aS)-8-benzenesulphonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-1,2-dicarboxylate

ethyl iodide

Downstream raw materials:

(αS)-1-benzenesulfonyl-α-ethyl-N_b-methoxycarbonyltryptophan methyl ester

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