(3S,3aS,7aR)-6-(2'-bromo-4'-methoxycyclohex-1'-enyl)-3-tert-butoxy-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene

Base Information

Chemical Name:(3S,3aS,7aR)-6-(2'-bromo-4'-methoxycyclohex-1'-enyl)-3-tert-butoxy-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene
CAS No.:679788-46-6
Molecular Formula:C₂₁H₃₃BrO₂
Molecular Weight:397.396
Hs Code.:

Synonyms:(3S,3aS,7aR)-6-(2'-bromo-4'-methoxycyclohex-1'-enyl)-3-tert-butoxy-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene

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Chemical Property of (3S,3aS,7aR)-6-(2'-bromo-4'-methoxycyclohex-1'-enyl)-3-tert-butoxy-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene

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Technology Process of (3S,3aS,7aR)-6-(2'-bromo-4'-methoxycyclohex-1'-enyl)-3-tert-butoxy-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene

There total 8 articles about (3S,3aS,7aR)-6-(2'-bromo-4'-methoxycyclohex-1'-enyl)-3-tert-butoxy-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene 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%

: 654667-51-3
2-bromo-4-methoxy-1-trifluoromethanesulfonyloxycyclohexene

: (1-tert-butoxy-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-5-yl)-tributyl-stannane

: 679788-46-6
(3S,3aS,7aR)-6-(2'-bromo-4'-methoxycyclohex-1'-enyl)-3-tert-butoxy-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene

Guidance literature:: With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; copper(l) iodide; triphenyl-arsane; lithium chloride; In 1-methyl-pyrrolidin-2-one; at 65 ℃; for 5h;
DOI:10.1002/anie.200352162

Reference yield:

: 654667-51-3
2-bromo-4-methoxy-1-trifluoromethanesulfonyloxycyclohexene

: 928758-66-1
(+)-(3S,3aS,7aR)-3-tert-butoxy-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-inden-6-yl trifluoromethanesulfonate

: 679788-46-6
(3S,3aS,7aR)-6-(2'-bromo-4'-methoxycyclohex-1'-enyl)-3-tert-butoxy-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene

Guidance literature:: (+)-(3S,3aS,7aR)-3-tert-butoxy-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-inden-6-yl trifluoromethanesulfonate; In tetrahydrofuran; at -78 - 20 ℃; for 4h;

2-bromo-4-methoxy-1-trifluoromethanesulfonyloxycyclohexene; With copper(l) iodide; lithium chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In 1-methyl-pyrrolidin-2-one; at 65 ℃; for 5h; Further stages.;
DOI:10.1002/chem.200601240

Reference yield:

: 943589-84-2
1,4-dimethoxycyclohexene

: 679788-46-6
(3S,3aS,7aR)-6-(2'-bromo-4'-methoxycyclohex-1'-enyl)-3-tert-butoxy-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene

Guidance literature:: Multi-step reaction with 3 steps

1.1: 73 percent / N-bromosuccinimide; sodium acetate / tetrahydrofuran; H₂O / 3 h / 22 °C

2.1: 92 percent / potassium hexamethyldisilazide / diethyl ether; toluene / 20 h / -78 - 20 °C

3.1: lithium cyano(bistributylstannyl)cuprate / tetrahydrofuran / 4 h / -78 - 20 °C

3.2: 497 mg / CuI; LiCl / [Pd₂(dba)3] / 1-methyl-pyrrolidin-2-one / 5 h / 65 °C

With N-Bromosuccinimide; sodium acetate; potassium hexamethylsilazane; In tetrahydrofuran; diethyl ether; water; toluene; 3.2: Stille coupling;
DOI:10.1002/chem.200601240