dimethyl (2S,3aR,8aS)-8-acetyl-5-phenyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

Base Information

Chemical Name:dimethyl (2S,3aR,8aS)-8-acetyl-5-phenyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate
CAS No.:161294-92-4
Molecular Formula:C₂₂H₂₂N₂O₅
Molecular Weight:394.427
Hs Code.:

Synonyms:dimethyl (2S,3aR,8aS)-8-acetyl-5-phenyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

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Chemical Property of dimethyl (2S,3aR,8aS)-8-acetyl-5-phenyl-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)-8-acetyl-5-phenyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

There total 1 articles about dimethyl (2S,3aR,8aS)-8-acetyl-5-phenyl-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: 64.0%

: 161294-91-3
dimethyl (2S,3aR,8aS)-8-acetyl-5-iodo-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

: 98-80-6
phenylboronic acid

: 161294-92-4
dimethyl (2S,3aR,8aS)-8-acetyl-5-phenyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

Guidance literature:: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 16h; Product distribution; other "catalyst" ; further arylboronic acid or B-alkyl-9-borabicyclo<3.3.1>nonane derivatives; alternative cross-coupling with acyclic 5-iodotryptophan analogue;
DOI:10.1055/s-1994-25708

Reference yield: 91.0%

: 161294-92-4
dimethyl (2S,3aR,8aS)-8-acetyl-5-phenyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

: 161294-99-1
N_b-methoxycarbonyl-5-phenyl-L-tryptophan methyl ester

Guidance literature:: With sulfuric acid; In methanol; for 3h; Ambient temperature;
DOI:10.1055/s-1994-25708

Reference yield:

: 161294-92-4
dimethyl (2S,3aR,8aS)-8-acetyl-5-phenyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

: 5-phenyl-L-tryptophan methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 91 percent / 20percent H₂SO₄ / methanol / 3 h / Ambient temperature

2: 83 percent / trimethylsilyl iodide / acetonitrile / 1 h / Heating

With trimethylsilyl iodide; sulfuric acid; In methanol; acetonitrile;
DOI:10.1055/s-1994-25708