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

Base Information

• Chemical Name: (+)-(2S,3aR,8aS)-1-(Methoxycarbonyl)-2-methyl-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-2-carboxylic acid
• CAS No.: 141870-93-1
• Molecular Formula: C₂₀H₂₀N₂O₆S
• Molecular Weight: 416.455
• Mol file: 141870-93-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about (+)-(2S,3aR,8aS)-1-(Methoxycarbonyl)-2-methyl-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-2-carboxylic acid 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: 93.0%

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) → (+)-(2S,3aR,8aS)-1-(Methoxycarbonyl)-2-methyl-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-2-carboxylic acid (141870-93-1)

Guidance literature:

With potassium hydroxide; In methanol; for 12h;

DOI:10.1021/jo00124a055

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) → (+)-(2S,3aR,8aS)-1-(Methoxycarbonyl)-2-methyl-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-2-carboxylic acid (141870-93-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) lithium diisopropylamide / 1) THF, hexane, -78 deg C, 20 min, 2) THF, hexane, to -60 deg C, 1 h

2: 72 percent / KOH / methanol; H₂O / 1 h / Ambient temperature

With potassium hydroxide; lithium diisopropyl amide; In methanol; water;

Reference yield:

L-(2β,3aα,8aα)-1,2,3,3a,8,8a-hexahydro-1,2-dimethoxycarbonylpyrrolo<2,3-b>indole (79465-82-0) → (+)-(2S,3aR,8aS)-1-(Methoxycarbonyl)-2-methyl-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-2-carboxylic acid (141870-93-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 62 percent / pyridine / 5 h / Ambient temperature

2: 1) lithium diisopropylamide / 1) THF, hexane, -78 deg C, 20 min, 2) THF, hexane, to -60 deg C, 1 h

3: 72 percent / KOH / methanol; H₂O / 1 h / Ambient temperature

With pyridine; potassium hydroxide; lithium diisopropyl amide; In methanol; water;

upstream raw materials:

dimethyl (2S,3aR,8aS)-2-methyl-8-phenylsulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo<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

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

benzenesulfonyl chloride

Downstream raw materials:

(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