(S)-1-Benzoyl-3a-((E)-3,7-dimethyl-octa-2,6-dienyl)-1,2,3,3a-tetrahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester

Base Information

Chemical Name:(S)-1-Benzoyl-3a-((E)-3,7-dimethyl-octa-2,6-dienyl)-1,2,3,3a-tetrahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester
CAS No.:863658-62-2
Molecular Formula:C₂₉H₃₂N₂O₃
Molecular Weight:456.585
Hs Code.:

Synonyms:(S)-1-Benzoyl-3a-((E)-3,7-dimethyl-octa-2,6-dienyl)-1,2,3,3a-tetrahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester

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Chemical Property of (S)-1-Benzoyl-3a-((E)-3,7-dimethyl-octa-2,6-dienyl)-1,2,3,3a-tetrahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester

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Technology Process of (S)-1-Benzoyl-3a-((E)-3,7-dimethyl-octa-2,6-dienyl)-1,2,3,3a-tetrahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester

There total 2 articles about (S)-1-Benzoyl-3a-((E)-3,7-dimethyl-octa-2,6-dienyl)-1,2,3,3a-tetrahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester 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: 83.0%

: 863658-61-1
1-benzoyl-1,2,3,8-tetrahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester

: 6138-90-5
trans-geranyl bromide

: 863658-62-2
(S)-1-Benzoyl-3a-((E)-3,7-dimethyl-octa-2,6-dienyl)-1,2,3,3a-tetrahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester

: (S)-1-Benzoyl-8-((E)-3,7-dimethyl-octa-2,6-dienyl)-1,2,3,8-tetrahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 0 ℃; for 5h; Title compound not separated from byproducts;
DOI:10.1016/j.tet.2006.06.074

Reference yield:

: 2717-75-1
N-benzoyl-L-tryptophan methyl ester

: 863658-62-2
(S)-1-Benzoyl-3a-((E)-3,7-dimethyl-octa-2,6-dienyl)-1,2,3,3a-tetrahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / Et₃N; t-BuOCl / CH₂Cl₂ / 13 h / 0 - 20 °C

2: 83 percent / NaH / tetrahydrofuran / 5 h / 0 °C

With tert-butylhypochlorite; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tet.2006.06.074

Reference yield:

: 863658-62-2
(S)-1-Benzoyl-3a-((E)-3,7-dimethyl-octa-2,6-dienyl)-1,2,3,3a-tetrahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester

: (2S,3aR,8aR)-3a-((E)-3,7-Dimethyl-octa-2,6-dienyl)-1-[(S)-3-phenyl-2-(2-trimethylsilanyl-ethoxycarbonylamino)-propionyl]-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 51 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h / -78 °C

2: 88 percent / aq.NaHCO₃ / dioxane / 2 h / 20 °C

3: catecholborane / tetrahydrofuran / 2 h / 0 °C

4: 202 mg / piperidine / acetonitrile / 1 h / 20 °C

5: 96 percent / Et₃N; HATU; HOAt / CH₂Cl₂ / 2 h / 0 °C

6: LiOH / tetrahydrofuran; methanol; H₂O / 1 h / 20 °C

With piperidine; lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; benzo[1,3,2]dioxaborole; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; acetonitrile;
DOI:10.1016/j.tet.2006.06.074