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

Base Information

• Chemical Name: dimethyl (2R,3aR,8aS)-2-(hydroxymethyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate
• CAS No.: 145814-46-6
• Molecular Formula: C₂₁H₂₂N₂O₇S
• Molecular Weight: 446.481

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

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

There total 2 articles about dimethyl (2R,3aR,8aS)-2-(hydroxymethyl)-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: 85.0%

dimethyl (2R,3aR,8aS)-8-(phenylsulfonyl)-2-<<2-(trimethylsilyl)ethoxy>methyl>-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (145814-41-1) → dimethyl (2R,3aR,8aS)-2-(hydroxymethyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (145814-46-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; for 1h;

DOI:10.1021/jm00055a001

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 (2R,3aR,8aS)-2-(hydroxymethyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (145814-46-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) lithium diisopropylamide (LDA) / 1.) THF, 1 h, 2.) THF, -78 deg C, 4 h

2: 85 percent / boron trifluoride etherate / CH₂Cl₂ / 1 h / 0 - 20 °C

With boron trifluoride diethyl etherate; lithium diisopropyl amide; In dichloromethane;

DOI:10.1021/jm00055a001

Reference yield: 50.0%

dimethyl (2R,3aR,8aS)-2-(hydroxymethyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (145814-46-6) → dimethyl (2R,3aR,8aS)-2-formyl-5-methoxy-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

Guidance literature:

With 3 A molecular sieve; pyridinium chlorochromate; In dichloromethane; for 6h; Ambient temperature;

DOI:10.1021/jm00055a001

upstream raw materials:

dimethyl (2R,3aR,8aS)-8-(phenylsulfonyl)-2-<<2-(trimethylsilyl)ethoxy>methyl>-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

Downstream raw materials:

α(S)-(fluoromethyl)tryptophan

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