ethyl 4-(3-azidopropyl)-1-(benzylcarbamothioyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinoline-8-carboxylate

Base Information

Chemical Name:ethyl 4-(3-azidopropyl)-1-(benzylcarbamothioyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinoline-8-carboxylate
CAS No.:1378383-53-9
Molecular Formula:C₂₅H₃₀N₆O₂S
Molecular Weight:478.618
Hs Code.:

Synonyms:ethyl 4-(3-azidopropyl)-1-(benzylcarbamothioyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinoline-8-carboxylate

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Chemical Property of ethyl 4-(3-azidopropyl)-1-(benzylcarbamothioyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinoline-8-carboxylate

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Technology Process of ethyl 4-(3-azidopropyl)-1-(benzylcarbamothioyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinoline-8-carboxylate

There total 3 articles about ethyl 4-(3-azidopropyl)-1-(benzylcarbamothioyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinoline-8-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: 81.0%

: 1378383-46-0
N-benzyl-2,3-dihydro-1H-pyrrole-1-carbothioamide

: 99545-47-8
4-azidobutanal

: 94-09-7
p-aminoethylbenzoate

: 1378383-53-9
ethyl 4-(3-azidopropyl)-1-(benzylcarbamothioyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinoline-8-carboxylate

Guidance literature:: 4-azidobutanal; p-aminoethylbenzoate; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;

N-benzyl-2,3-dihydro-1H-pyrrole-1-carbothioamide; With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; In dichloromethane; at -30 ℃; for 15h; optical yield given as %ee; stereoselective reaction; Inert atmosphere;
DOI:10.1002/chem.201200523

Reference yield:

: 305791-50-8
N-benzyl-2-oxopyrrolidine-1-carbothioamide

: 1378383-53-9
ethyl 4-(3-azidopropyl)-1-(benzylcarbamothioyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinoline-8-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: lithium triethylborohydride / tetrahydrofuran; toluene / 0.5 h / -70 °C / Inert atmosphere

1.2: 2 h / -70 - 20 °C / Inert atmosphere

2.1: dichloromethane / 0.5 h / 20 °C / Inert atmosphere

2.2: 15 h / -30 °C / Inert atmosphere

With lithium triethylborohydride; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1002/chem.201200523

Reference yield:

: 622-78-6
Benzyl isothiocyanate

: 1378383-53-9
ethyl 4-(3-azidopropyl)-1-(benzylcarbamothioyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinoline-8-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: lithium triethylborohydride / tetrahydrofuran; toluene / 0.5 h / -70 °C / Inert atmosphere

2.2: 2 h / -70 - 20 °C / Inert atmosphere

3.1: dichloromethane / 0.5 h / 20 °C / Inert atmosphere

3.2: 15 h / -30 °C / Inert atmosphere

With sodium hydride; lithium triethylborohydride; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1002/chem.201200523