Dimethyl 2,3-methano-8-(phenylsulfonyl)-1,2(S),3(S),3a(R),8,8a(S)-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

Base Information

• Chemical Name: Dimethyl 2,3-methano-8-(phenylsulfonyl)-1,2(S),3(S),3a(R),8,8a(S)-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate
• CAS No.: 145642-89-3
• Molecular Formula: C₂₁H₂₀N₂O₆S
• Molecular Weight: 428.466
• Mol file: 145642-89-3.mol

Synonyms:Dimethyl 2,3-methano-8-(phenylsulfonyl)-1,2(S),3(S),3a(R),8,8a(S)-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

Chemical Property of Dimethyl 2,3-methano-8-(phenylsulfonyl)-1,2(S),3(S),3a(R),8,8a(S)-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Dimethyl 2,3-methano-8-(phenylsulfonyl)-1,2(S),3(S),3a(R),8,8a(S)-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

There total 4 articles about Dimethyl 2,3-methano-8-(phenylsulfonyl)-1,2(S),3(S),3a(R),8,8a(S)-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: 56.0%

trimethylsulfoxonium iodide (1774-47-6) + Dimethyl 8-(phenylsulfonyl)-1,3a(R),8,8a(S)-tetrahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (145642-80-4) → Dimethyl 2,3-methano-8-(phenylsulfonyl)-1,2(S),3(S),3a(R),8,8a(S)-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (145642-89-3)

Guidance literature:

With sodium methylsulfinylmethanide; In dimethyl sulfoxide; Ambient temperature;

DOI:10.1016/S0040-4039(00)60945-0

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) → Dimethyl 2,3-methano-8-(phenylsulfonyl)-1,2(S),3(S),3a(R),8,8a(S)-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (145642-89-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / LDA / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) -78 deg C, 60 min then -78 deg C to r.t.

2: 99 percent / MMPP / tetrahydrofuran / 3 h / Ambient temperature

3: 56 percent / NaH, DMSO / 1.) 2.5 h, 2.) r.t., 5 h

With sodium hydride; dimethyl sulfoxide; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1021/jo00094a041

Reference yield:

Dimethyl 2-(phenylseleno)-8-(phenylsulfonyl)-1,2(R),3,3a(R),8,8a(S)-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (145642-79-1) → Dimethyl 2,3-methano-8-(phenylsulfonyl)-1,2(S),3(S),3a(R),8,8a(S)-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (145642-89-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / MMPP / tetrahydrofuran / 3 h / Ambient temperature

2: 56 percent / NaH, DMSO / 1.) 2.5 h, 2.) r.t., 5 h

With sodium hydride; dimethyl sulfoxide; In tetrahydrofuran;

DOI:10.1021/jo00094a041

upstream raw materials:

trimethylsulfoxonium iodide

Dimethyl 8-(phenylsulfonyl)-1,3a(R),8,8a(S)-tetrahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

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

Dimethyl 2-(phenylseleno)-8-(phenylsulfonyl)-1,2(R),3,3a(R),8,8a(S)-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

Downstream raw materials:

erythro-α,β-methano-N-(methoxycarbonyl)-1-(phenylsulfonyl)-L-tryptophan methyl ester