(3aS,8aR)-3a-ethyl-1,2,3,3a,8,8a-hexahydro-1,8-dimethyl-5-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolo[2,3-b]indole

Base Information

Chemical Name:(3aS,8aR)-3a-ethyl-1,2,3,3a,8,8a-hexahydro-1,8-dimethyl-5-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolo[2,3-b]indole
CAS No.:1314797-98-2
Molecular Formula:C₂₂H₂₅N₅
Molecular Weight:359.474
Hs Code.:

Synonyms:(3aS,8aR)-3a-ethyl-1,2,3,3a,8,8a-hexahydro-1,8-dimethyl-5-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolo[2,3-b]indole

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Chemical Property of (3aS,8aR)-3a-ethyl-1,2,3,3a,8,8a-hexahydro-1,8-dimethyl-5-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolo[2,3-b]indole

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Technology Process of (3aS,8aR)-3a-ethyl-1,2,3,3a,8,8a-hexahydro-1,8-dimethyl-5-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolo[2,3-b]indole

There total 6 articles about (3aS,8aR)-3a-ethyl-1,2,3,3a,8,8a-hexahydro-1,8-dimethyl-5-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolo[2,3-b]indole 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: 80.0%

: 1313809-96-9
(3aS,8aR)-5-azido-3a-ethyl-1,8-dimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole

: 536-74-3
phenylacetylene

: 1314797-98-2
(3aS,8aR)-3a-ethyl-1,2,3,3a,8,8a-hexahydro-1,8-dimethyl-5-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolo[2,3-b]indole

Guidance literature:: With copper(l) iodide; sodium ascorbate; In N,N-dimethyl-formamide; at 20 ℃; for 4h; regioselective reaction; Inert atmosphere;
DOI:10.1002/hlca.201100020

Reference yield:

: 1313810-17-1
(3aS,8aR)-3a-ethyl-5-iodo-1,8-dimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole

: 1314797-98-2
(3aS,8aR)-3a-ethyl-1,2,3,3a,8,8a-hexahydro-1,8-dimethyl-5-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolo[2,3-b]indole

Guidance literature:: Multi-step reaction with 2 steps

1: copper(l) iodide; sodium azide; sodium ascorbate; N,N`-dimethylethylenediamine / water; dimethyl sulfoxide / 24 h / 20 °C / Inert atmosphere

2: copper(l) iodide; sodium ascorbate / N,N-dimethyl-formamide / 4 h / 20 °C / Inert atmosphere

With copper(l) iodide; sodium azide; sodium ascorbate; N,N`-dimethylethylenediamine; In water; dimethyl sulfoxide; N,N-dimethyl-formamide; 2: Huisgen reaction;
DOI:10.1002/hlca.201100020

Reference yield:

: 1313810-16-0
(3aS,8aS)-methyl 8-methyl-3a-(3-oxopropyl)-3,3a,8,8a-tetrahydropyrrolo[2,3-b]indole-1(2H)-carboxylate

: 1314797-98-2
(3aS,8aR)-3a-ethyl-1,2,3,3a,8,8a-hexahydro-1,8-dimethyl-5-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolo[2,3-b]indole

Guidance literature:: Multi-step reaction with 5 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux

2: Raney-Ni / toluene / Reflux

3: N-iodo-succinimide / dichloromethane / 0 - 20 °C

4: copper(l) iodide; sodium azide; sodium ascorbate; N,N`-dimethylethylenediamine / water; dimethyl sulfoxide / 24 h / 20 °C / Inert atmosphere

5: copper(l) iodide; sodium ascorbate / N,N-dimethyl-formamide / 4 h / 20 °C / Inert atmosphere

With N-iodo-succinimide; copper(l) iodide; lithium aluminium tetrahydride; sodium azide; sodium ascorbate; N,N`-dimethylethylenediamine; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 5: Huisgen reaction;
DOI:10.1002/hlca.201100020