(1aS,7bS)-1a-benzyl-3-((trifluoromethyl)sulfonyl)-1a,2,3,7b-tetrahydro-1H-cyclopropa[c]quinoline

Base Information

Chemical Name:(1aS,7bS)-1a-benzyl-3-((trifluoromethyl)sulfonyl)-1a,2,3,7b-tetrahydro-1H-cyclopropa[c]quinoline
CAS No.:1448600-19-8
Molecular Formula:C₁₈H₁₆F₃NO₂S
Molecular Weight:367.392
Hs Code.:

Synonyms:(1aS,7bS)-1a-benzyl-3-((trifluoromethyl)sulfonyl)-1a,2,3,7b-tetrahydro-1H-cyclopropa[c]quinoline

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Chemical Property of (1aS,7bS)-1a-benzyl-3-((trifluoromethyl)sulfonyl)-1a,2,3,7b-tetrahydro-1H-cyclopropa[c]quinoline

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Technology Process of (1aS,7bS)-1a-benzyl-3-((trifluoromethyl)sulfonyl)-1a,2,3,7b-tetrahydro-1H-cyclopropa[c]quinoline

There total 4 articles about (1aS,7bS)-1a-benzyl-3-((trifluoromethyl)sulfonyl)-1a,2,3,7b-tetrahydro-1H-cyclopropa[c]quinoline 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: 99.0%

: 1448600-02-9
N-((1-benzylcyclopropyl)methyl)-N-(2-bromophenyl)-1,1,1-trifluoromethanesulfonamide

: 1448600-19-8
(1aS,7bS)-1a-benzyl-3-((trifluoromethyl)sulfonyl)-1a,2,3,7b-tetrahydro-1H-cyclopropa[c]quinoline

Guidance literature:: With (1R,7R)-4-dimethylamino-9,9-dimethyl-2,2,6,6-tetra(3,5-dimethylphenyl)-3,5,8,10-tetraoxa-4-phosphabicyclo[5.3.0]decane; caesium carbonate; bis(dibenzylideneacetone)-palladium⁽⁰⁾; Trimethylacetic acid; In para-xylene; at 130 ℃; for 12h; enantioselective reaction; Inert atmosphere;
DOI:10.1002/anie.201207959

Reference yield:

: 27356-91-8
1-benzylcyclopropanecarboxylic acid

: 1448600-19-8
(1aS,7bS)-1a-benzyl-3-((trifluoromethyl)sulfonyl)-1a,2,3,7b-tetrahydro-1H-cyclopropa[c]quinoline

Guidance literature:: Multi-step reaction with 5 steps

1.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

3.1: borane-THF / tetrahydrofuran / 8 h / Reflux; Inert atmosphere

4.1: sodium hydride / 1,2-dichloro-ethane / 0 - 20 °C / Inert atmosphere

5.1: (1R,7R)-4-dimethylamino-9,9-dimethyl-2,2,6,6-tetra(3,5-dimethylphenyl)-3,5,8,10-tetraoxa-4-phosphabicyclo[5.3.0]decane; bis(dibenzylideneacetone)-palladium⁽⁰⁾; Trimethylacetic acid; caesium carbonate / para-xylene / 12 h / 130 °C / Inert atmosphere

With (1R,7R)-4-dimethylamino-9,9-dimethyl-2,2,6,6-tetra(3,5-dimethylphenyl)-3,5,8,10-tetraoxa-4-phosphabicyclo[5.3.0]decane; borane-THF; oxalyl dichloride; sodium hydride; caesium carbonate; triethylamine; N,N-dimethyl-formamide; bis(dibenzylideneacetone)-palladium⁽⁰⁾; Trimethylacetic acid; In tetrahydrofuran; dichloromethane; para-xylene; 1,2-dichloro-ethane;
DOI:10.1002/anie.201207959

Reference yield:

: 105676-90-2
1-Benzylcyclopropancarbonylchlorid

: 1448600-19-8
(1aS,7bS)-1a-benzyl-3-((trifluoromethyl)sulfonyl)-1a,2,3,7b-tetrahydro-1H-cyclopropa[c]quinoline

Guidance literature:: Multi-step reaction with 4 steps

1.1: triethylamine / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: borane-THF / tetrahydrofuran / 8 h / Reflux; Inert atmosphere

3.1: sodium hydride / 1,2-dichloro-ethane / 0 - 20 °C / Inert atmosphere

4.1: (1R,7R)-4-dimethylamino-9,9-dimethyl-2,2,6,6-tetra(3,5-dimethylphenyl)-3,5,8,10-tetraoxa-4-phosphabicyclo[5.3.0]decane; bis(dibenzylideneacetone)-palladium⁽⁰⁾; Trimethylacetic acid; caesium carbonate / para-xylene / 12 h / 130 °C / Inert atmosphere

With (1R,7R)-4-dimethylamino-9,9-dimethyl-2,2,6,6-tetra(3,5-dimethylphenyl)-3,5,8,10-tetraoxa-4-phosphabicyclo[5.3.0]decane; borane-THF; sodium hydride; caesium carbonate; triethylamine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; Trimethylacetic acid; In tetrahydrofuran; dichloromethane; para-xylene; 1,2-dichloro-ethane;
DOI:10.1002/anie.201207959