(2S,3S,3aR,8aS)-8-Benzyl-3a-(1-benzyl-1H-indol-3-yl)-3-methoxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methylamide

Base Information

Chemical Name:(2S,3S,3aR,8aS)-8-Benzyl-3a-(1-benzyl-1H-indol-3-yl)-3-methoxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methylamide
CAS No.:926011-01-0
Molecular Formula:C₃₅H₃₄N₄O₂
Molecular Weight:542.681
Hs Code.:

Synonyms:(2S,3S,3aR,8aS)-8-Benzyl-3a-(1-benzyl-1H-indol-3-yl)-3-methoxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methylamide

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Chemical Property of (2S,3S,3aR,8aS)-8-Benzyl-3a-(1-benzyl-1H-indol-3-yl)-3-methoxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methylamide

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Technology Process of (2S,3S,3aR,8aS)-8-Benzyl-3a-(1-benzyl-1H-indol-3-yl)-3-methoxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methylamide

There total 13 articles about (2S,3S,3aR,8aS)-8-Benzyl-3a-(1-benzyl-1H-indol-3-yl)-3-methoxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methylamide 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: 65.0%

: 926011-00-9
8-benzyl-3a-(1-benzyl-1H-indol-3-yl)-3-methoxy-2-methylcarbamoyl-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid tert-butyl ester

: 926011-01-0
(2S,3S,3aR,8aS)-8-Benzyl-3a-(1-benzyl-1H-indol-3-yl)-3-methoxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methylamide

Guidance literature:: With trimethylsilyl iodide; In acetonitrile; at 0 ℃; for 0.666667h;
DOI:10.1021/ol062801y

Reference yield:

: 860653-34-5
(S)-3-((1S,2R)-2-Amino-1,3-dihydroxy-propyl)-1,1'-dibenzyl-1,3-dihydro-1'H-[3,3']biindolyl-2-one

: 926011-01-0
(2S,3S,3aR,8aS)-8-Benzyl-3a-(1-benzyl-1H-indol-3-yl)-3-methoxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methylamide

Guidance literature:: Multi-step reaction with 12 steps

1: 1.85 g / camphorsulfonic acid / benzene / 3 h / 50 °C

2: 93 percent / LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

3: 91 percent / diisopropylethylamine / CH₂Cl₂ / 48 h / 20 °C

4: 100 percent / Na₂CO₃ / tetrahydrofuran; H₂O / 2 h / 20 °C

5: 71 percent / oxalic acid / methanol / 1 h / 20 °C

6: 96 percent / NaH / tetrahydrofuran / 2 h / 20 °C

7: 77 percent / NaI / tetrahydrofuran / 2 h / 0 - 20 °C

8: 92 percent / tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 20 °C

9: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C

10: 2-methyl-2-butene; NaH₂PO₄*H₂O; NaClO₂ / tetrahydrofuran; H₂O / 2 h / 20 °C

11: 38.1 mg / triethylamine; benzotriazole-1-yloxy-tris(dimethylamino)phosphonium*PF₆^(1-) / CH₂Cl₂ / 3 h / 20 °C

12: 65 percent / TMSI / acetonitrile / 0.67 h / 0 °C

With pyridine; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; 2-methyl-but-2-ene; trimethylsilyl iodide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; oxalic acid; sodium hydride; sodium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; benzene; 9: Dess-Martin oxidation;
DOI:10.1021/ol062801y

Reference yield:

: 860653-35-6
3-(5-amino-2,2-dimethyl-[1,3]dioxan-4-yl)-1,1'-dibenzyl-1,3-dihydro-1'H-[3,3']biindolyl-2-one

: 926011-01-0
(2S,3S,3aR,8aS)-8-Benzyl-3a-(1-benzyl-1H-indol-3-yl)-3-methoxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methylamide

Guidance literature:: Multi-step reaction with 11 steps

1: 93 percent / LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

2: 91 percent / diisopropylethylamine / CH₂Cl₂ / 48 h / 20 °C

3: 100 percent / Na₂CO₃ / tetrahydrofuran; H₂O / 2 h / 20 °C

4: 71 percent / oxalic acid / methanol / 1 h / 20 °C

5: 96 percent / NaH / tetrahydrofuran / 2 h / 20 °C

6: 77 percent / NaI / tetrahydrofuran / 2 h / 0 - 20 °C

7: 92 percent / tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 20 °C

8: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C

9: 2-methyl-2-butene; NaH₂PO₄*H₂O; NaClO₂ / tetrahydrofuran; H₂O / 2 h / 20 °C

10: 38.1 mg / triethylamine; benzotriazole-1-yloxy-tris(dimethylamino)phosphonium*PF₆^(1-) / CH₂Cl₂ / 3 h / 20 °C

11: 65 percent / TMSI / acetonitrile / 0.67 h / 0 °C

With pyridine; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; 2-methyl-but-2-ene; trimethylsilyl iodide; tetrabutyl ammonium fluoride; oxalic acid; sodium hydride; sodium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; 8: Dess-Martin oxidation;
DOI:10.1021/ol062801y