(2β,3α)-(+/-)-2-benzyl-3-(trimethylstannyl)cyclohexanone

Base Information

Chemical Name:(2β,3α)-(+/-)-2-benzyl-3-(trimethylstannyl)cyclohexanone
CAS No.:130762-05-9
Molecular Formula:C₁₆H₂₄OSn
Molecular Weight:351.076
Hs Code.:

Synonyms:(2β,3α)-(+/-)-2-benzyl-3-(trimethylstannyl)cyclohexanone

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Chemical Property of (2β,3α)-(+/-)-2-benzyl-3-(trimethylstannyl)cyclohexanone

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Technology Process of (2β,3α)-(+/-)-2-benzyl-3-(trimethylstannyl)cyclohexanone

There total 2 articles about (2β,3α)-(+/-)-2-benzyl-3-(trimethylstannyl)cyclohexanone 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: 80.0%

: 930-68-7
cyclohexenone

: 661-69-8
hexamethyldistannane

: 100-39-0
benzyl bromide

: 130762-05-9
(2β,3α)-(+/-)-2-benzyl-3-(trimethylstannyl)cyclohexanone

Guidance literature:: With methyllithium; In tetrahydrofuran; diethyl ether; N2 atmosphere; addn. of soln. of MeLi in Et2O to soln. of Me6Sn2 (0°C), stirring (0°C, 15 min), addn. of soln. of 2-cyclohexenone in THF, stirring (0°C, 1 h), addn. of benzyl bromide, stirring (0°C, 20 min); pouring into H2O, extn (Et2O), drying (MgSO4), concn, , chromy. (silica gel, hexane and 9:1 hexane/ethyl acetate);

Reference yield: 73.0%

: 109-72-8,29786-93-4
n-butyllithium

: 72170-87-7
(+)-(2S)-N-[cyclohex-2-en-1-yliden]-2-(methoxymethyl)pyrrolidin-1-amine

: 661-69-8
hexamethyldistannane

: 130762-05-9
(2β,3α)-(+/-)-2-benzyl-3-(trimethylstannyl)cyclohexanone

Guidance literature:: With benzyliodide or bromide; O₃; In tetrahydrofuran; addn. of distannane to n-BuLi, cooling after 2 h to -100°C, warming to -78°C, dropwise addn. of the pyrrolidine compd., addn. of Alk-X, evapn., dissolving in Et2O, washing (H2O, satd. NaCl), concn. and ozonolysis (CH2Cl2, -78°C); removing of the O3 with Ar, warming, evapn. and column chromy. (silica gel, petroleum ether-Et2O); de 98 %, ee 96 %;

Reference yield:

: 16940-66-2
sodium tetrahydroborate

: 130762-05-9
(2β,3α)-(+/-)-2-benzyl-3-(trimethylstannyl)cyclohexanone

: 128162-15-2
(1β,2β,3α)-(+/-)-2-benzyl-3-(trimethylstannyl)-1-cyclohexanol

: 128095-28-3
(1β,2β,3α)-(+/-)-2-benzyl-3-(trimethylstannyl)-1-cyclohexanol

Guidance literature:: In methanol; addn. of soln. of Sn-compd. in MeOH to NaBH4 (0°C), stirring (0°C, 30 min); addn. of dild. HCL, extn. (Et2O), drying (Na2SO4), concn., dissoln. (CH2Cl2), filtration (alumina), removal of CH2Cl2, sepn. of isomer mixt. on chromy. (silica gel, 7:3 hexane/ethyl acetate);