(S)-(E)-tert-butyl 6-(4-cyclohexyl-2-((methylcarbamoyl)thio)but-3-en-2-yl)-1H-indole-1-carboxylate

Base Information

Chemical Name:(S)-(E)-tert-butyl 6-(4-cyclohexyl-2-((methylcarbamoyl)thio)but-3-en-2-yl)-1H-indole-1-carboxylate
CAS No.:1613417-30-3
Molecular Formula:C₂₅H₃₄N₂O₃S
Molecular Weight:442.623
Hs Code.:

Synonyms:(S)-(E)-tert-butyl 6-(4-cyclohexyl-2-((methylcarbamoyl)thio)but-3-en-2-yl)-1H-indole-1-carboxylate

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Chemical Property of (S)-(E)-tert-butyl 6-(4-cyclohexyl-2-((methylcarbamoyl)thio)but-3-en-2-yl)-1H-indole-1-carboxylate

Chemical Property:

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Technology Process of (S)-(E)-tert-butyl 6-(4-cyclohexyl-2-((methylcarbamoyl)thio)but-3-en-2-yl)-1H-indole-1-carboxylate

There total 11 articles about (S)-(E)-tert-butyl 6-(4-cyclohexyl-2-((methylcarbamoyl)thio)but-3-en-2-yl)-1H-indole-1-carboxylate 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:

: 5318-27-4
6-amino-1H-indole

: (R)-(E)-tert-butyl 6-(4-cyclohexyl-2-((methylcarbamoyl)thio)but-3-en-2-yl)-1H-indole-1-carboxylate

: 1613417-30-3
(S)-(E)-tert-butyl 6-(4-cyclohexyl-2-((methylcarbamoyl)thio)but-3-en-2-yl)-1H-indole-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: pyridine / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 °C / Reflux; Inert atmosphere

3.1: benzotriazol-1-ol / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere; Reflux

4.1: triethylamine; dmap / dichloromethane / 20 h / 20 °C / Inert atmosphere

5.1: diisopropylamine; lithium chloride; n-butyllithium / tetrahydrofuran / -78 - -60 °C / Inert atmosphere

5.2: -78 - 20 °C / Inert atmosphere

With pyridine; dmap; lithium aluminium tetrahydride; n-butyllithium; benzotriazol-1-ol; triethylamine; diisopropylamine; lithium chloride; In tetrahydrofuran; dichloromethane;
DOI:10.1039/c4cc02596b

Reference yield:

: 1613417-10-9
(S)-(E)-tert-butyl 6-((((4-cyclohexylbut-3-en-2-yl)thio)carbonyl)(methyl)amino)-1H-indole-1-carboxylate

: (R)-(E)-tert-butyl 6-(4-cyclohexyl-2-((methylcarbamoyl)thio)but-3-en-2-yl)-1H-indole-1-carboxylate

: 1613417-30-3
(S)-(E)-tert-butyl 6-(4-cyclohexyl-2-((methylcarbamoyl)thio)but-3-en-2-yl)-1H-indole-1-carboxylate

Guidance literature:: (S)-(E)-tert-butyl 6-((((4-cyclohexylbut-3-en-2-yl)thio)carbonyl)(methyl)amino)-1H-indole-1-carboxylate; With n-butyllithium; diisopropylamine; lithium chloride; In tetrahydrofuran; at -78 - -60 ℃; Inert atmosphere;

With propionic acid; In tetrahydrofuran; at -78 - 20 ℃; Overall yield = 41 %; Overall yield = 24 mg; Inert atmosphere;
DOI:10.1039/c4cc02596b

Reference yield:

: 79646-42-7,106499-63-2,120849-47-0,130930-52-8,18736-82-8,137764-95-5,79605-62-2
(E)-1-cyclohexyl-2-buten-1-ol

: (R)-(E)-tert-butyl 6-(4-cyclohexyl-2-((methylcarbamoyl)thio)but-3-en-2-yl)-1H-indole-1-carboxylate

: 1613417-30-3
(S)-(E)-tert-butyl 6-(4-cyclohexyl-2-((methylcarbamoyl)thio)but-3-en-2-yl)-1H-indole-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: dmap / 1,2-dichloro-ethane / 26 h / 40 °C / Inert atmosphere

2.1: benzotriazol-1-ol / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere; Reflux

3.1: triethylamine; dmap / dichloromethane / 20 h / 20 °C / Inert atmosphere

4.1: diisopropylamine; lithium chloride; n-butyllithium / tetrahydrofuran / -78 - -60 °C / Inert atmosphere

4.2: -78 - 20 °C / Inert atmosphere

With dmap; n-butyllithium; benzotriazol-1-ol; triethylamine; diisopropylamine; lithium chloride; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane;
DOI:10.1039/c4cc02596b