(1R,4R)-spiro[5-trifluoromethanesulfonyloxybicyclo[2.2.1]hept-5-ene-2,2'-[1,3]dioxolane]

Base Information

Chemical Name:(1R,4R)-spiro[5-trifluoromethanesulfonyloxybicyclo[2.2.1]hept-5-ene-2,2'-[1,3]dioxolane]
CAS No.:608489-09-4
Molecular Formula:C₁₀H₁₁F₃O₅S
Molecular Weight:300.256
Hs Code.:

Synonyms:(1R,4R)-spiro[5-trifluoromethanesulfonyloxybicyclo[2.2.1]hept-5-ene-2,2'-[1,3]dioxolane]

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Chemical Property of (1R,4R)-spiro[5-trifluoromethanesulfonyloxybicyclo[2.2.1]hept-5-ene-2,2'-[1,3]dioxolane]

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Technology Process of (1R,4R)-spiro[5-trifluoromethanesulfonyloxybicyclo[2.2.1]hept-5-ene-2,2'-[1,3]dioxolane]

There total 4 articles about (1R,4R)-spiro[5-trifluoromethanesulfonyloxybicyclo[2.2.1]hept-5-ene-2,2'-[1,3]dioxolane] 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%

: 145100-50-1
1,1,1-trifluoro-N-(pyridin-2-yl)-N-((trifluoromethyl)sulfonyl)methane sulfonamide

: 608489-08-3
(1R,4R)-spiro[bicyclo[2.2.1]heptan-5-one-2,2'-[1.3]dioxolane]

: 608489-09-4,1352718-74-1
(1R,4R)-spiro[5-trifluoromethanesulfonyloxybicyclo[2.2.1]hept-5-ene-2,2'-[1,3]dioxolane]

Guidance literature:: (1R,4R)-spiro[bicyclo[2.2.1]heptan-5-one-2,2'-[1.3]dioxolane]; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

1,1,1-trifluoro-N-(pyridin-2-yl)-N-((trifluoromethyl)sulfonyl)methane sulfonamide; In tetrahydrofuran; hexane; at -78 - 20 ℃;
DOI:10.1021/ja037367z

Reference yield:

: 135094-36-9
(1R,2S,4R,5S)-exo,exo-bicyclo[2.2.1]heptane-2,5-diol

: 608489-09-4,1352718-74-1
(1R,4R)-spiro[5-trifluoromethanesulfonyloxybicyclo[2.2.1]hept-5-ene-2,2'-[1,3]dioxolane]

Guidance literature:: Multi-step reaction with 3 steps

1.1: Me₂SO; (COCl)2; Et₃N / CH₂Cl₂

2.1: TsOH

3.1: n-BuLi; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 °C

3.2: 81 percent / tetrahydrofuran; hexane / -78 - 20 °C

With n-butyllithium; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; 1.1: Swern oxidation;
DOI:10.1021/ja037367z

Reference yield:

: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

: 608489-09-4,1352718-74-1
(1R,4R)-spiro[5-trifluoromethanesulfonyloxybicyclo[2.2.1]hept-5-ene-2,2'-[1,3]dioxolane]

Guidance literature:: Multi-step reaction with 4 steps

1.1: HSiCl3; [PdCl(π-C3H5)2]; (R)-MeO-MOP / 0 °C

1.2: Et₃N / methanol

1.3: aq. H₂O₂; KHF₂ / tetrahydrofuran; methanol

2.1: Me₂SO; (COCl)2; Et₃N / CH₂Cl₂

3.1: TsOH

4.1: n-BuLi; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 °C

4.2: 81 percent / tetrahydrofuran; hexane / -78 - 20 °C

With (Ra)-(2'-methoxy-[1,1']-binaphthalenyl-2-yl)-diphenylphosphine; n-butyllithium; oxalyl dichloride; bis(η3-allyl-μ-chloropalladium(II)); trichlorosilane; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; 2.1: Swern oxidation;
DOI:10.1021/ja037367z