dimethyl (2S,3aR,8aS)-2-methyl-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-methyl-8-phenylsulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate
• CAS No.: 141870-92-0
• Molecular Formula: C₂₁H₂₂N₂O₆S
• Molecular Weight: 430.481
• Mol file: 141870-92-0.mol

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

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

There total 4 articles about dimethyl (2S,3aR,8aS)-2-methyl-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:

L-(2β,3aα,8aα)-1,2,3,3a,8,8a-hexahydro-1,2-dimethoxycarbonylpyrrolo<2,3-b>indole (79465-82-0) → dimethyl (2S,3aR,8aS)-2-methyl-8-phenylsulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (141870-92-0)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine

2: 1.) LDA

With lithium diisopropyl amide; In pyridine;

DOI:10.1016/0040-4020(95)00001-O

Reference yield:

Nα-methoxycarbonyl-D-tryptophan methyl ester (79631-04-2) → dimethyl (2S,3aR,8aS)-2-methyl-8-phenylsulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (141870-92-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 85percent H₃PO₄

2: pyridine

3: 1.) LDA

With phosphoric acid; lithium diisopropyl amide; In pyridine;

DOI:10.1016/0040-4020(95)00001-O

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) + methyl iodide (74-88-4) → dimethyl (2S,3aR,8aS)-2-methyl-8-phenylsulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (141870-92-0)

Guidance literature:

With lithium diisopropyl amide; Yield given. Multistep reaction; 1) THF, -78 deg C;

DOI:10.1016/S0040-4039(00)92648-0

upstream raw materials:

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

methyl iodide

N_α-methoxycarbonyl-D-tryptophan methyl ester

L-(2β,3aα,8aα)-1,2,3,3a,8,8a-hexahydro-1,2-dimethoxycarbonylpyrrolo<2,3-b>indole

Downstream raw materials:

(S)-3-(1-Benzenesulfonyl-1H-indol-3-yl)-2-methoxycarbonylamino-2-methyl-propionic acid methyl ester

(+)-(2S,3aR,8aS)-1-(Methoxycarbonyl)-2-methyl-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-2-carboxylic acid

C₂₁H₂₁BrN₂O₆S

(2S,3aR,8aS)-8-Benzenesulfonyl-2-isobutoxycarbonyloxycarbonyl-2-methyl-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid methyl ester