(Z)-3-(1-(tert-butyldimethylsilyloxy)-2-cyclohexylvinyl)oxazolidin-2-one

Base Information

Chemical Name:(Z)-3-(1-(tert-butyldimethylsilyloxy)-2-cyclohexylvinyl)oxazolidin-2-one
CAS No.:1330660-52-0
Molecular Formula:C₁₇H₃₁NO₃Si
Molecular Weight:325.524
Hs Code.:

Synonyms:(Z)-3-(1-(tert-butyldimethylsilyloxy)-2-cyclohexylvinyl)oxazolidin-2-one

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Chemical Property of (Z)-3-(1-(tert-butyldimethylsilyloxy)-2-cyclohexylvinyl)oxazolidin-2-one

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Technology Process of (Z)-3-(1-(tert-butyldimethylsilyloxy)-2-cyclohexylvinyl)oxazolidin-2-one

There total 2 articles about (Z)-3-(1-(tert-butyldimethylsilyloxy)-2-cyclohexylvinyl)oxazolidin-2-one 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: 64.0%

: 497143-73-4
3-(2-cyclohexylethanoyl)oxazolidin-2-one

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1330660-52-0
(Z)-3-(1-(tert-butyldimethylsilyloxy)-2-cyclohexylvinyl)oxazolidin-2-one

Guidance literature:: 3-(2-cyclohexylethanoyl)oxazolidin-2-one; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

tert-butyldimethylsilyl chloride; In tetrahydrofuran; hexane; at 20 ℃; for 12h; Inert atmosphere;
DOI:10.1021/ja206050b

Reference yield:

: 23860-35-7
cyclohexylacetic acid chloride

: 1330660-52-0
(Z)-3-(1-(tert-butyldimethylsilyloxy)-2-cyclohexylvinyl)oxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

2.2: 12 h / 20 °C / Inert atmosphere

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane;
DOI:10.1021/ja206050b

Reference yield:

: 1330660-52-0
(Z)-3-(1-(tert-butyldimethylsilyloxy)-2-cyclohexylvinyl)oxazolidin-2-one

: 58109-40-3
diphenyliodonium hexafluorophosphate

: 1330660-75-7
(S)-3-(2-cyclohexyl-2-phenylethanoyl)oxazolidin-2-one

: (R)-3-(2-cyclohexyl-2-phenylethanoyl)oxazolidin-2-one

Guidance literature:: With [((CH₃)2C(C₃H₃NOC₆H₅)2)Cu(OSO₂CF₃)]; CuOTf*1/2PhMe; In dichloromethane; toluene; at 5 ℃; for 24h; optical yield given as %ee; enantioselective reaction;
DOI:10.1021/ja206050b