9-benzoyl-4-(trifluoromethylsulfonyloxy)-1-methyl-9-azabicyclo[3.3.1]non-3-ene

Base Information

Chemical Name:9-benzoyl-4-(trifluoromethylsulfonyloxy)-1-methyl-9-azabicyclo[3.3.1]non-3-ene
CAS No.:470669-11-5
Molecular Formula:C₁₇H₁₈F₃NO₄S
Molecular Weight:389.395
Hs Code.:

Synonyms:9-benzoyl-4-(trifluoromethylsulfonyloxy)-1-methyl-9-azabicyclo[3.3.1]non-3-ene

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Chemical Property of 9-benzoyl-4-(trifluoromethylsulfonyloxy)-1-methyl-9-azabicyclo[3.3.1]non-3-ene

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Technology Process of 9-benzoyl-4-(trifluoromethylsulfonyloxy)-1-methyl-9-azabicyclo[3.3.1]non-3-ene

There total 14 articles about 9-benzoyl-4-(trifluoromethylsulfonyloxy)-1-methyl-9-azabicyclo[3.3.1]non-3-ene 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: 63.0%

: 145100-51-2
N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide

: 470669-30-8
9-benzoyl-1-methyl-9-azabicyclo[3.3.1]nonan-4-one

: 470669-11-5
9-benzoyl-4-(trifluoromethylsulfonyloxy)-1-methyl-9-azabicyclo[3.3.1]non-3-ene

Guidance literature:: 9-benzoyl-1-methyl-9-azabicyclo[3.3.1]nonan-4-one; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide; In tetrahydrofuran; hexane; at -20 - 20 ℃;
DOI:10.1039/b203243k

Reference yield:

: 132910-79-3
(+/-) methyl N-tert-butyloxycarbonyl 2-piperidinecarboxylate

: 470669-11-5
9-benzoyl-4-(trifluoromethylsulfonyloxy)-1-methyl-9-azabicyclo[3.3.1]non-3-ene

Guidance literature:: Multi-step reaction with 14 steps

1.1: LiN(SiMe₃)2 / tetrahydrofuran / -78 °C

1.2: tetrahydrofuran

2.1: LiAlH₄ / diethyl ether

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂

4.1: BuLi / tetrahydrofuran

5.1: H₂ / 10 percent Pd/C / ethyl acetate / 5 kg/cm²

6.1: LiAlH₄ / diethyl ether

7.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂

8.1: PPh₃; t-BuOK / toluene

9.1: BuLi; TMEDA / tetrahydrofuran / -78 °C

9.2: tetrahydrofuran

10.1: Et₃N; DMAP / benzene

11.1: 95 percent / Bu₃SnH; AIBN / toluene / 2 h / Heating

12.1: 89 percent / CF₃COOH / CH₂Cl₂ / 0.25 h / 0 °C

13.1: O₃ / CH₂Cl₂ / 0.17 h / -78 °C

13.2: 71 percent / PPh₃ / CH₂Cl₂ / 0.25 h / 20 °C

14.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C

14.2: 63 percent / tetrahydrofuran; hexane / -20 - 20 °C

With dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); N,N,N,N,-tetramethylethylenediamine; potassium tert-butylate; hydrogen; tri-n-butyl-tin hydride; ozone; dimethyl sulfoxide; triethylamine; triphenylphosphine; trifluoroacetic acid; lithium hexamethyldisilazane; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; toluene; benzene; 3.1: Swern oxidation / 4.1: Horner-Emmons reaction / 7.1: Swern oxidation;
DOI:10.1039/b203243k

Reference yield:

: 470669-16-0
2-formyl-2-methyl-piperidine-1-carboxylic acid tert-butyl ester

: 470669-11-5
9-benzoyl-4-(trifluoromethylsulfonyloxy)-1-methyl-9-azabicyclo[3.3.1]non-3-ene

Guidance literature:: Multi-step reaction with 11 steps

1.1: BuLi / tetrahydrofuran

2.1: H₂ / 10 percent Pd/C / ethyl acetate / 5 kg/cm²

3.1: LiAlH₄ / diethyl ether

4.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂

5.1: PPh₃; t-BuOK / toluene

6.1: BuLi; TMEDA / tetrahydrofuran / -78 °C

6.2: tetrahydrofuran

7.1: Et₃N; DMAP / benzene

8.1: 95 percent / Bu₃SnH; AIBN / toluene / 2 h / Heating

9.1: 89 percent / CF₃COOH / CH₂Cl₂ / 0.25 h / 0 °C

10.1: O₃ / CH₂Cl₂ / 0.17 h / -78 °C

10.2: 71 percent / PPh₃ / CH₂Cl₂ / 0.25 h / 20 °C

11.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C

11.2: 63 percent / tetrahydrofuran; hexane / -20 - 20 °C

With dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); N,N,N,N,-tetramethylethylenediamine; potassium tert-butylate; hydrogen; tri-n-butyl-tin hydride; ozone; dimethyl sulfoxide; triethylamine; triphenylphosphine; trifluoroacetic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; toluene; benzene; 1.1: Horner-Emmons reaction / 4.1: Swern oxidation;
DOI:10.1039/b203243k